The Operations Room: A Podcast for COO’s

In this episode we ask the unpack the question of: Do COO's have a two year shelf life? We discussed this topic with Casey Woo, CEO @Operators Guild. 

We discuss the following with Casey: 

• What is the role of the COO? 
• Why does the COO have a two year shelf life? 
• If that is the reality, how should one think about their career? 
• What does this mean for 4 year option grants? 
• What are the key terms every COO should negotiate? 

References

• www.operators-guild.com
• https://summit.operators-guild.com/2024

Biography: 

Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups. 

Casey now leads 800+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance and operations roles. He believes strongly that community is what makes the difference for start-ups and professionals. 

When he’s not working, Casey is spending time in California’s Bay Area with his wife and three children. 

Summary:

• CEO shelf life and software frustrations. 0:06
• Brandon and Bethany discuss their least favorite piece of software, with Brandon naming Microsoft Teams as his least favorite and Bethany agreeing due to its poor performance on Macs.
• Both agree that the entire Microsoft suite, including Word, has always been problematic and frustrating to use.
• Bethany and Brandon discuss the pros and cons of Google Docs and Microsoft 365 for collaboration, with Bethany preferring Google Docs for its ease of use and collaboration features.
• Brandon shares his experience of transitioning from Microsoft to Google Docs, finding it difficult to adjust to the new platform but ultimately appreciating its collaboration capabilities.
• Bethany: Transition from growth to optimization occurs around 50 million in revenue and 250 employees.
• Brandon: First two phases of growth and commercialization are enjoyable, but third phase of optimization is less enjoyable and happens around 50 million in revenue and 250 employees.
• Communicating option value to employees and talent acquisition teams. 7:57
• Bethany suggests using a product like Lecce to help employees understand the value of their options and how they vest over time.
• Brandon agrees that communicating the value of options as part of compensation is important, and notes that their company could have done a better job of this in the past.
• Brandon and Bethany discuss the importance of educating employees on option grants and their value, including providing a clear framework for career progression and regular updates on the terms and benefits of option grants.
• Casey Woo, founder of the Operator's Guild, shares his experience of implementing option grants for employees, including tying them to job role and seniority, and providing awards for top performers to increase their options.
• CEO role and responsibilities. 12:50
• Casey Woo shares insights from 35,000 hours of listening and talking to CEOs, highlighting the diverse reasons why people want to be CEOs, including wide impact and not being a CFO or salesperson.
• Woo challenges the common view of CEOs as a single role, emphasizing the various perspectives and responsibilities held by CEOs in different companies and stages of growth.
• Casey Woo argues that a CEO's role is not just one person, but rather a complement to the CEO and a gap filler.
• CEO roles, decision-making, and power dynamics. 16:53
• CEOs face unique challenges, including rapidly changing roles and delicate power dynamics with other executives.
• Casey Woo emphasizes the importance of clear decision-making roles and responsibilities in a CEO-founder relationship, avoiding confusion and undermining the CEO's authority.
• Bethany agrees, citing decision-making power as a common challenge, particularly with founder CEOs, and discussing strategies to address it.
• Bethany and Casey discuss the role of a CEO in a scale-up company, with Bethany advocating for a two-year vesting schedule and Casey suggesting a step-two approach to becoming a CRO or CFO.
• Casey emphasizes the importance of understanding the expectations and limitations of a two-year CEO role, and how it can lead to a more successful transition to a permanent position.
• Stock options in the UK and US, with insights on vesting schedules, taxes, and exercise windows. 24:01
• Bethany learned that cliff vesting options, where only a portion of options vest after a certain time, was common in the UK 10-15 years ago but is no longer used.
• Bethany and Casey Woo discussed the challenges of stock options, including high exercise costs, limited time windows, and uneven vesting schedules.
• Options for early-stage companies in the UK and US. 26:33
• Brandon and Casey discuss the differences in UK and US options laws, with the UK offering lower strike prices and longer exercise windows.
• Casey argues that it's employee-friendly for companies to offer longer exercise windows, as early-stage companies need time to reach value.
• Options negotiation and key considerations. 29:03
• Bethany and Casey Woo discuss the importance of negotiating options and understanding the terms, including strike price, vesting, and good lever provisions.
• They emphasize the value of having a clear understanding of these terms to protect one's interests and maximize the potential of options.
• Equity compensation and career growth for scale-ups. 31:18
• Brandon recommends revising the Articles of Association to ensure board discretionary ownership doesn't affect an entrepreneur's livelihood.
• Casey Woo agrees and adds that double trigger or single trigger acceleration of vesting is important for operators and senior operators in the event of a change of control.
• Casey Woo emphasizes the importance of understanding the stage of a company and its evolution when negotiating compensation and setting career goals.
• Casey encourages listeners to be realistic about their expectations and to transform and exit the company within a set timeframe, rather than staying for an extended period without achieving goals.

In this episode we unpack the topic of: Leadership Transitions: Uncompromising Strategies for Success with Andrew Duncan, Talent @ Atomico (ex-UpGroup) and Maddy Cross Partner @ Erevena (ex-Notion Capital)

We discuss the following with Maddy and Andrew: 

• Given the average tenure of senior execs in scaleups, what advice would you give execs and what should companies that are hiring consider? 
• How uncompromising do you need to be to get the right leaders in place?
• What is the difference in leadership skills needed between early and late stage? 
• Do we need someone that has been there and done that? 
• What is the right mix of experience needed for a leadership team? 
• How do you identify gaps in a leadership team?  

References

• Barry McCarthy (story mentioned by Andrew)
• Former Netflix CFO Barry McCarthy Joins Super-Secretive Payments Startup Clinkle As COO
• Clinkle's Still a Hot Mess as Its Big Shot COO Departs
• Clinkle Up In Smoke As Investors Want Their Money Back
• The COO role (giving context for how Andrew thinks about the role)
• Stepping up: What COOs will need to succeed in 2023 and beyond
• Second in Command: The Misunderstood Role of the Chief Operating Officer
• How Best To Onboard Into Different Types Of COO Role
• What is a Chief Operating Officer? 
• From the beginning to a billion. How unicorns built their leadership teams (mentioned by Maddy)
• What to Look for in Your VC's Talent Arm (mentioned by Brandon and loved by Maddy)
• How to Understand the ROI of Investing in People (wasn’t mentioned but Maddy thinks is a great piece)

Biography: 

Maddy Cross is a Partner at Erevena, an Executive Search firm focussed on investor backed businesses, where she leads the European Technology and Engineering practice for B2B. Previously she was Talent Director at Notion Capital, a $1bn B2B SaaS focussed VC, and she holds an MBA from London Business School.

Andrew is a Talent Director at Atomico, one of Europe's largest venture capital funds. He supports portfolio companies in finding and hiring elite executive talent and is responsible for advising founders on the evolution of their leadership teams. Previously, he spent time building executive teams while at Kindred Partners (San Francisco) and The Up Group (London).

Summary: 

• Cannabis legalization in the UK. 0:06
• Bethany Ayers discusses her frustration with the UK's lack of progress in legalizing cannabis, citing the ease of access and variety of strains available in the US.
• Brandon Mensing agrees, noting that alcohol is often used as a stress reliever in the evening but can have negative effects on the body.
• Bethany researches cannabis for blood sugar control and weight loss, finding limited evidence but potential benefits for women.
• UK legalized cannabis for medical use five years ago, but limited access and high costs for patients.
• Bethany and Brandon discuss leadership transitions with Andrew Duncan and Maddie Krause, with a focus on the ideal tenure for executives (2-4 years) and how to handle executives with shorter tenures.
• Maddie shares advice on how to handle executives who have experienced a shorter tenure than they would have wanted, emphasizing the importance of empathy and support.
• CMO tenure and leadership in enterprise software companies. 8:03
• Duncan notes short tenures for CMOs in tech, but highlights successful cases.
• Executive tenure and its impact on career growth. 9:45
• Maddie Cross and Andrew Duncan discuss the nuances of being asked to leave a business, with Maddie sharing examples of sensitive departures where people have stayed in the company for years after being asked to leave their original role.
• Andrew adds that for senior execs, especially those later in their careers, market timing can play a role in their ability to find new opportunities, and talent professionals should consider this when evaluating candidates.
• Both Maddie and Andrew emphasize the importance of handling departures with sensitivity and respect, and providing support to help people move on to new opportunities.
• Maddie Cross highlights the importance of considering tenure in the context of each function, as marketing and people roles tend to have shorter tenures in high-growth b2b software companies.
• Andrew Duncan asks if the same tenure standards apply across functions, with CFOs having shorter tenures due to their specific roles and responsibilities.
• Leadership decisions and ruthlessness in business. 15:49
• Andrew Duncan and Brandon discuss the importance of assessing someone's background and experience to determine their fit for a business, and the potential for short tenure in leadership positions.
• Maddie Cross emphasizes the need for ruthless decision-making in leadership positions, but also stresses the importance of being direct and constructive in those decisions.
• Managing a business during a downturn. 18:57
• Founders, investors, and executives are having harder conversations about business performance and course of action.
• Bethany and Maddie discuss the challenges of making difficult decisions as a founder, including sequencing and taking advice from trusted individuals.
• Maddie suggests breaking down the decision-making process into smaller, more manageable steps to avoid feeling overwhelmed and making no decisions at all.
• Leadership skills and expectations at different stages of a company's growth. 22:31
• Andrew Duncan notes that companies have had to develop internal communications plans to effectively communicate sensitive decisions to their organizations, particularly in the last 12-18 months.
• Bethany asks Andrew about fundamental changes in skills and expectations at the BC-D to IPO stage, and what leaders bring to the table.
• Andrew Duncan: Executives in later stages may prioritize process management over working in the business.
• Bethany: Communication and delegation become more challenging in later stages, with many layers between leaders and those doing work.
• Leadership team composition and diversity. 27:47
• Maddie Cross suggests having a mix of experienced leaders and up-and-coming talent on a leadership team for a healthy balance of perspectives and skills.
• Brandon agrees and adds that a mix of both types of individuals can provide a more well-rounded leadership team, with the caveat that everyone needs to know their role and responsibilities.
• Maddie Cross analyzed two groups of b2b software companies: unicorns (valued at over $2B) and less successful ones.
• Key differences between the two groups include the range of years of prior experience (tighter delta in less successful companies) and educational background (more people from top universities in successful companies).
• Leadership team gaps and hiring decisions in early-stage companies. 32:33
• Andrew Duncan emphasizes the importance of trusted leaders in early-stage companies, even if they haven't held similar roles in other businesses.
• He highlights the need to balance proven track record with potential risks when bringing in outside execs at later stages of growth.
• Founders should consider a mix of people with and without prior experience in their role to bring diverse perspectives.
• Identify gaps in a leadership team by clearly defining North Star goals and assessing confidence in assigning them to team members.
• Use a combination of internal and external resources to surround functional heads with people who can increase their likelihood of success, such as mentors, boot camps, or other trusted individuals.
• Hiring and leadership for venture-backed companies. 38:48
• Key capabilities need to exist in a business for a successful series B fundraising round, and a strong leader must be responsible for those capabilities.
• For B2B SaaS businesses, a strong sales leader is crucial for fundraising, while a CFO with extensive experience may not be as critical.
• Maddie Cross advises not letting fear of making hiring mistakes hold you back, while Andrew Duncan highlights the importance of contingency planning for executive success.
• Andrew Duncan and Maddie Cross discuss the importance of accepting risks in building venture-backed companies, sharing examples of successful executives who have made mistakes.

In this episode we unpack the topic of: "Cracking the Code: Exploring Emotional Literacy and Embodiment” This is Part 2 in our emotional literacy and embodiment series. Our special guests are returning alumni with Divinia Knowles, Founder of the COO Roundtable and Maddie Fox, a leadership development coach across venture-backed organisations. We are also joined by Pippa Richardson, Somatic Therapist, Educator, Speaker and Clinician. 

We discuss the following with Pippa, Maddie and Divinia: 

• Our personal journey’s into embodiment
• What do we disconnect from our body? 
• What is dysregulation? 
• How do you manage through a day of back-to-back meetings? 
• How do you bring embodiment into the day-to-day? 

Biography: 

Pippa is a highly regarded Somatic Therapist, Educator, Speaker and Clinician. She has lived experience and clinical expertise in the areas of trauma, eating disorders, addiction, recovery and healing. With over 10 years experience of working and studying in the field of embodiment, body-centred therapies and psychosomatics, both in clinical and non-clinical settings. Her work lies at the intersection of psyche (mind) and soma (body) and she is passionate about supporting her clients to live an embodied, meaningful life. 

Alongside her clinical work, Pippa leads talks, retreats and workshops both in the UK and abroad. She has a broad range of experience working with individuals, groups and organisations including the US Military, Save The Children, Bamford, Manolo Blahnik - as well as with leadership executives and professional athletes. Her work aims to provide thought provoking environments to explore the human experience with curiosity, kindness and compassion.

Divinia was COO, CFO & a director at both Mind Candy and Pact Coffee, where she also served as interim CEO.  She has held or still holds chair and board seats at too many companies to list and is occasionally an angel investor. Divinia re-trained as a coach in 2017 and combined it with her previous experience to become the COO Coach, working with start up/scale up COOs/CEOs to help guide them through successfully starting up, scaling up and exiting. And in addition to all that, she is also the Founder of the London COO Roundtable, a community that brings operations professionals together to define what it means to be a highly effective startup and scale up Chief Operating Officer.

Divinia Knowles references

COO Roundtable - https://www.cooroundtable.com/

LinkedIn - https://www.linkedin.com/in/diviniaknowles/

Divinia’s email - [email protected]

Maddie has over 20 years experience in HR and Learning & Development working with various organizations from corporate to fast growing tech, in Europe, the US and Australia. She is an ICF accredited executive coach, leadership and HR consultant with a wide range of experience, however specialising in developing leaders from emerging leaders to seasoned CEO’s, building high-performing sustainable teams and helping clients successfully navigate change. Her style is eclectic, using research, theory and direct experiences to ensure individuals find ways to effectively embed new behaviours, build resilience and deliver results. More recently she has been working in VC backed start-ups, series A-B, working for mostly founder led businesses as a Chief People Officer, Leadership Coach and Advisor. Clients include Blippar, Lantum, Trint, Mixcloud, amongst others. 

Summary:

• Diversity and inclusivity in tech industry. 0:05
• Bethany shares her experience at an EQ event for people and talent, feeling like an imposter among mostly women in leadership roles.
• People and talent leadership, strategic conversations, and IT budgets. 2:13
• Bethany highlights the importance of the people team being involved in strategic decision-making and having a seat at the leadership table.
• Brandon agrees, emphasizing the need for people leaders to be proactive in thinking through the implications of choices made by the leadership team, particularly in terms of human resources and operations.
• Brandon and Bethany discuss the importance of people leaders having control over their IT budgets and understanding people ops and analytics to run the business effectively.
• Bethany suggests that combining thinking and feeling perspectives can create a powerful combination for business success.
• Embodiment and acting techniques for emotional connection. 7:00
• Brandon struggles with abstract concept of embodiment, citing communication issues in his career.
• Brandon discovered that traditional communications training was ineffective and found acting classes to be more helpful in understanding the human condition and connecting with others.
• The Meisner technique, which includes the repetition exercise, was instrumental in Brandon's acting development and ability to connect with others on stage.
• Brandon describes Meisner technique as "mesmerizing" and "emotionally difficult" but ultimately "spectacular" for connecting with others.
• Bethany shares how she discovered her body through acting and wants to hear others' experiences to inspire new ways of embodiment.
• Somatic practice and its connection to leadership and emotions. 14:10
• Divinia bumps into Nick Kitchen, an executive coach with a somatic practice, and learns about the disconnect between people's words and body language during team coaching supervision.
• Somatic therapy and body awareness. 15:44
• Pippa realized she was disconnected from her body through somatic therapy, leading to profound life changes.
• Embodied coaching and somatic practices. 18:22
• Maddie's curiosity about the body and mind led her to explore somatic coaching, which she found helpful in connecting with her body and sensations.
• Maddie notes that while Pilates can be a helpful exercise practice, it's possible to do it in an objectified way that's disconnected from the body, and that somatic coaching offers a more embodied approach to movement and self-awareness.
• Therapy, embodiment, and yoga for body positivity. 21:01
• Bethany finds solace in yoga after years of therapy, feeling more grounded and centered.
• Bethany discovers joy in embodiment through PIPA, undoing years of yoga conditioning.
• Disconnection from body and its impact on society. 24:48
• Pippa argues that disconnection from the body can limit connection and joy, and is reinforced by systemic factors.
• Body awareness and dysregulation. 26:18
• Maddie and Divinia discuss the importance of recognizing and addressing unregulated stress in the body, which can lead to physical sensations like pain or anxiety.
• Divinia explains that unregulated stress can manifest in various ways, including physical sensations, behaviors, and emotions, and that it's important to identify and release this stored trauma to move forward.
• Autonomic nervous system and stress regulation. 29:22
• Pippa references autonomic nervous system, explaining sympathetic (accelerator) and parasympathetic (brake) states, and how body signals can indicate stress or anticipation.
• Dysregulation occurs when the body's stress response system becomes overloaded, leading to difficulty regulating emotions and behaviors.
• Managing energy and presence in meetings. 32:38
• Maddie suggests incorporating intentional pauses between meetings to improve presence and productivity.
• Brandon and Maddie discuss the challenges of maintaining energy and focus throughout the workday, particularly for senior executives.
• Maddie suggests practices outside of work, such as yoga or exercise, can help increase resilience and presence in meetings.
• Categorizing daily tasks based on energy levels. 36:24
• Reflect on energy-giving activities to prioritize in daily work.
• Self-care and body awareness. 37:49
• Bethany prioritizes self-care by giving herself permission to do what feels good in her body, such as laying flat on the ground for a couple of minutes each day.
• Somatic practices for stress reduction and self-awareness. 38:51
• Practice dual awareness of self and others to reduce stress levels.
• Resilience coaching and grounding exercises. 41:18
• Divinia observes that using words like "presence" can be misleading, as people may not actually be as present as they think.
• Somatic coaching and its benefits for stress management. 42:40
• Maddie and Bethany discuss the importance of centering practices for managing stress and difficult interactions, and Maddie leads a quick centering exercise to demonstrate the technique.
• The exercise involves bringing to mind a difficult interaction, physically sensing any tension in the body, and then grounding oneself through a scan up the body and attention to familiar places.
• Maddie guides listeners to find space in their body by centering themselves and lengthening from the crown of the head to the soles of their feet.
• Pippa, Bethany, and Brandon discuss the importance of creating space and having more choice in our bodies and actions, leading to a more conscious and intentional approach to life.

In this episode we unpack the topic of: "Cracking the Code: Exploring Emotional Literacy and Embodiment” This is Part 1 in our emotional literacy and embodiment series. Our special guests are returning alumni with Divinia Knowles, Founder of the COO Roundtable and Maddie Fox, a leadership development coach across venture-backed organisations. 

Bethany and I discuss the concept of “reading the room” and “the pause”. 

We discuss the following with Maddie and Divinia: 

• How far can you push as a challenger COO to the CEO? 
• What is emotional literacy and embodiment? 
• How do you move from your head and into your body
• Can you have emotional literacy without embodiment? 
• Is embodiment a personal journey? If so, what does that mean? 
• How do you stop yourself from taking on other people's emotions? 
• What was your personal journey to embodied leadership? 

References:

COO Roundtable - https://www.cooroundtable.com/

LinkedIn - https://www.linkedin.com/in/diviniaknowles/

Divinia’s email - [email protected]

Biography: 

Divinia was COO, CFO & a director at both Mind Candy and Pact Coffee, where she also served as interim CEO.  She has held or still holds chair and board seats at too many companies to list and is occasionally an angel investor. Divinia re-trained as a coach in 2017 and combined it with her previous experience to become the COO Coach, working with start up/scale up COOs/CEOs to help guide them through successfully starting up, scaling up and exiting. And in addition to all that, she is also the Founder of the London COO Roundtable, a community that brings operations professionals together to define what it means to be a highly effective startup and scale up Chief Operating Officer.

Maddie has over 20 years experience in HR and Learning & Development working with various organizations from corporate to fast growing tech, in Europe, the US and Australia. She is an ICF accredited executive coach, leadership and HR consultant with a wide range of experience, however specialising in developing leaders from emerging leaders to seasoned CEO’s, building high-performing sustainable teams and helping clients successfully navigate change. Her style is eclectic, using research, theory and direct experiences to ensure individuals find ways to effectively embed new behaviours, build resilience and deliver results. More recently she has been working in VC backed start-ups, series A-B, working for mostly founder led businesses as a Chief People Officer, Leadership Coach and Advisor. Clients include Blippar, Lantum, Trint, Mixcloud, amongst others. 

Summary:

• Emotional intelligence and leadership in the workplace. 0:05
• Brandon and Bethany discuss emotional literacy and embodied leadership with guests Devaney and Maddy, focusing on reading the room in tense team situations and galvanizing the wider organization around new initiatives.
• Reading the room in meetings. 1:31
• Bethany and Brandon discuss leadership skills in meetings, with Bethany focusing on reading the room and Brandon using a surprising tactic to get teams to work together.
• Participants in a meeting shared their emotions using a "vibe check" technique, allowing for a more empathetic and understanding atmosphere.
• Emotional preparation for presentations and leadership. 4:47
• Brandon emphasizes emotional preparation for presentations to connect with audience.
• Actors tap into true emotion by embodiment, leading to powerful connections with others.
• Embodiment and pausing to manage emotions. 8:07
• Brandon and Bethany discuss the concept of creating a pause in emotional situations to think about new options and respond thoughtfully, rather than react impulsively.
• Bethany shares her personal journey of discovering how to pause and choose her responses, rather than reacting instinctively, through therapy and embodiment practices.
• Bethany felt angry and frustrated about a decision made by her company's head of marketing, and she expressed her feelings by pacing and feeling her physical sensations.
• Bethany eventually realized that her anger was not about the specific decision, but about feeling disempowered and unheard in her role.
• Bethany shares her experience of self-imposed torture due to misinterpreted emotions in a board meeting.
• Giving feedback to founders in a supportive manner. 14:33
• Maddie and Bethany discuss the best approach to giving feedback to founders, including waiting for the right opportunity and being perceptive to the founder's needs.
• Bethany shares her experience of observing and waiting for the right moment to give feedback, rather than scheduling a specific meeting.
• Emotional intelligence in leadership roles. 16:41
• Divinia emphasizes emotional literacy as a crucial aspect of leadership, highlighting the importance of understanding one's own emotions and being able to articulate them in a constructive manner.
• Embodied leadership and emotional literacy. 18:25
• Emotional literacy is key for leaders to read the room better, as they often don't know how to name their own emotions or understand others'.
• Bethany shares her personal experience with embodied leadership, mentioning she went to a yoga class religiously for a year and a half but hasn't done yoga since.
• Maddie shares a conference example where she incorporated embodied practices and received positive feedback from some attendees, highlighting the importance of setting seeds for future understanding.
• Emotional intelligence in leadership teams. 22:44
• Divinia notes that many leaders live in their heads and struggle to connect with their own feelings, leading to a lack of emotional intelligence in leadership teams.
• Divinia uses embodied practices and emotions wheels to help leaders articulate and understand their emotions, creating a common language for the team.
• Embodied leadership and commitment. 25:16
• Maddie highlights the importance of embodied leadership, where a leader's commitment is reflected in their body language and actions.
• Personal growth through embodied leadership. 26:28
• Bethany shares her personal journey of embodied leadership, from impatience to patience and calmer environments.
• Embodiment and emotional literacy in a work environment. 28:19
• Divinia and Bethany discuss the challenge of embodiment without emotional literacy in a work environment.
• Embodiment and emotional literacy in leadership development. 30:02
• Maddie discusses the concept of embodiment in leadership, highlighting the importance of being fully present and aware in high-pressure situations.
• She argues that practicing embodied leadership allows individuals to pause and make conscious choices in response to challenges, rather than defaulting to habitual reactions.
• Maddie provides an example of a leader she coached who improved their emotional literacy and relationships by practicing somatic practices, becoming more curious and open to others.
• Embracing body leadership and emotional expression in business. 34:17
• Bethany shares her personal journey of embracing her body and emotions in leadership, finding abundance and presence in meetings.
• The challenges of embodied leadership. 35:48
• Divinia notes the complexity of being an embodied leader, open to others' emotions while maintaining effectiveness.
• Empathy and emotional overflow in helping others. 37:11
• Brandon struggles with taking on others' emotions, leading to burnout and decreased empathy.
• Self-care for leaders in high-stress work environments. 38:16
• Leaders must prioritize self-care to avoid burnout and lead effectively.
• Coaching, emotional expression, and leadership development. 40:09
• Divinia shares her journey of understanding the importance of resilience practices in coaching, emphasizing the need to recognize and respect clients' emotions.
• Bethany seeks advice on how to help others start their own transformational journeys, acknowledging that there is no one-size-fits-all approach.
• Personal growth and leadership development. 42:53
• Maddie and Divinia share their personal experiences with self-awareness and personal growth work, highlighting the importance of taking time for oneself and recognizing the impact on all areas of life.
• Divinia shares her journey of self-discovery through coaching, from early experiences with a functional leadership team to later struggles with dysfunctional teams and personal emotional takeovers.
• Divinia highlights the transformative impact of coaching, including sessions with her founders coach, Penny, and personal training in Gestalt, embodied somatic, and TA practices.
• Embodied leadership and community-building. 46:33
• 
  
• Bethany seeks community for embodied leadership practice, feels lonely.

In this episode we unpack the topic of: "Transitioning Roles: From COO to CEO". This is Part 2 in our transitioning roles series. Our special guest is John Saroff, CEO of Chartbeat. 

Bethany and I discuss what a CEO does, and how a COO can build competence in these areas: 

• Vision
• Fundraising
• Board relationships
• Setting the tone for the culture

We then discuss the following with John: 

• What is the role of a CEO and how does it differ to the COO role?
• Do you have a COO now? Why not? 
• How does the stress of the CEO role differ to the COO? 
• As someone who has suffered from depression, how has that influenced your time as CEO? 
• What do you wish you would have known when you transitioned from COO to CEO? 
• When you transitioned into the CEO role, did you struggle with role definition? 
• When is a COO ready to take the CEO role? 
• How do you become emotionally available to employees? 

References

• Chartbeat

Biography: 

John Saroff is Chief Executive Officer of Chartbeat, Inc., an ecosystem of enterprise solutions that enables media companies to grow reach and revenue. Chartbeat serves more that 1,000 brands globally, including The New York Times, BBC, ESPN, BuzzFeed, Paramount, Warner Bros., Hearst, and McClatchy. The company brings together Chartbeat, the industry-leading content analytics software for digital publishers; Tubular Labs, a comprehensive analytics solution that delivers a unified view of social video audiences; and Lineup Systems, a bespoke tool for providing media companies with revenue management software. John has worked on the cutting-edge of media and technology for 24 years, at companies ranging from Google to NBC. He holds a joint degree in law and business from Columbia University and is a graduate of Haverford College.

Summary:

• Career development and CEO transitions. 0:06
• Bethany shares how she spent her 20s experimenting with different identities and careers, feeling less ashamed about her lack of progress.
• Brandon: Inspired by Pierre Trudeau's career path, he pursued various manual labor jobs in his 20s without a clear career goal, focusing on enjoying life and graduating from university.
• John Saref: As CEO of Chartbeat, he transitioned from Google and NBC Universal, discussing how a CEO can build competence by galvanizing the organization and stakeholders around the company's vision, mission, and purpose.
• Leadership, vision, and communication skills for CEOs. 3:32
• Bethany emphasizes the importance of having a clear and compelling vision as a leader, which she believes is essential for inspiring others to work towards a common goal.
• Brandon agrees that vision is crucial, but also acknowledges that it can be challenging for ordinary people to articulate a powerful storyline in a way that is both competent and charismatic.
• Brandon: Product background helps with vision and storytelling (black slide technique)
• Bethany: Keep presentations simple and focused on the future (no bullet points, no visuals)
• CEO responsibilities and skills. 7:40
• Bethany and Brandon both played key roles in fundraising rounds, learning investor thinking and complementing the CEO's strengths with their own areas of expertise.
• Fundraising is like another sales cycle, requiring collaboration and pairing off with different people to add value and secure investment.
• Bethany emphasizes the importance of communication and empathy for CEOs in investor relations and customer meetings.
• Bethany and Brandon discuss the importance of building relationships as a CEO, with Bethany emphasizing the value of having a strong relationship with key stakeholders.
• Bethany and Brandon also touch on the topic of setting the tone for the company culture, with Bethany noting that as CEO, you are setting the tone rather than just toeing the party line.
• Career transition from corporate lawyer to content acquisition at NBC. 14:19
• John Saroff transitioned from corporate lawyer to content acquisition at NBC after feeling unfulfilled and depressed in his law career.
• He networked extensively and interviewed with 26 people for the job, eventually getting hired by Mike Stipe, who is still a close friend.
• Saroff emphasizes the importance of finding a career that aligns with one's passions and values, rather than simply chasing the "brass ring" of partnership.
• CEO responsibilities and stress. 17:21
• John Saroff, former COO, describes the difference between the CEO and COO roles as "enormous" and "really different," respectively.
• John Saroff does not currently have a COO, having taken over as CEO after his predecessor left to start a company sold to Twitter.
• John Saroff describes the stress of being a CEO, comparing it to being the "least bad choice" with a small team and limited resources.
• CEO stress, depression, and mental health resources. 21:00
• John Saroff highlights the stress-reducing aspects of being a CEO, such as having ultimate decision-making authority and being accountable for the company's success or failure.
• Bethany agrees, noting that the lack of authority to make decisions without the CEO's approval can be immensely stressful for team members.
• John Saroff discusses his struggles with depression as a corporate lawyer and how he found support through therapy and medication.
• He emphasizes the importance of mental health resources for employees and stigmatizing mental illness in the workplace.
• Saroff shares his success story of managing depression and anxiety, encouraging others to seek help.
• Leadership, vision, and growth as a CEO. 26:19
• Bethany shares her struggles with perfectionism and feeling like she didn't measure up in her 20s, despite being high achiever.
• Brandon contrasts their backgrounds, sharing how he didn't have a full-time job until age 28 and didn't have traditional experience, but found success as a CEO.
• John Saroff reflects on his early days as CEO, realizing the importance of having a clear vision and mission for the company.
• He emphasizes the need to identify what the company is the best in the world at, and how it can move the economic engine and fire up employees.
• CEO role and coaching employees. 30:59
• John Saroff describes his CEO role as a "very involved coach" drawing on experiences from college leadership roles.
• John Saroff emphasizes the importance of coaching and communication as a CEO, using examples from his experience as a Liverpool fan and a New York Giants fan.
• Saroff believes that meddling can be healthy if employees understand why the CEO is involved, citing the example of a client who only tells the CEO the truth.
• CEO mindset, emotional intelligence, and self-care. 34:45
• John Saroff emphasizes the importance of self-awareness and emotional reserves for CEOs, citing it as a key trait for success in the role.
• Bethany highlights the need for CEOs to be able to operationalize and inspire their teams, while also taking on ultimate accountability.
• John Saroff emphasizes the importance of taking care of oneself holistically to be successful in any field, especially as a CEO.
• He practices active listening and reminds himself that his opinions are just that, while acknowledging the feelings and opinions of others.
• John encourages listeners to take action and make the transition to their desired career, emphasizing that it only takes one "yes" to make it happen.

In this episode we unpack the topic of: "Transitioning Roles: From COO to Venture Capitalist". This is Part 1 of a two-part series. Our special guest is Cleo Sham, Venture Partner at StrideVC. We discuss the following: 

• Why did you decide to move from operator to investor? 
• How did being an operator inform your role as a VC? 
• Where did you find joy in the COO role? As a VC?
• Which role is more stressful: COO or VC? 
• When you received critical feedback as a leader, how did you deal with it? 
• How do you carve out quality thinking time with so many diverse opportunities? 
• How would a COO make the move to VC? 

Biography: 

Before joining Stride as an investor, I had built and led teams as a scale-up operator across China and EMEA. 

I joined Uber as one of the first GMs on the ground in China in 2014, building the Guangzhou business into Uber's largest city by volume globally and led China National Operations up until Uber China's $35B merger with Didi Chuxing in 2016. I subsequently moved to Amsterdam as EMEA Director of Operations to lead the platformization of Uber's ridesharing business across 45 countries.

Relocating to London in 2019, I took on the COO role at Spotahome after their $40M Series B, led by Bond Capital. Spotahome is a b2b2c mid-term rentals marketplace, and there I transformed and led a ±200 person team across sales, marketing, operations, strategy, and customer support.

I love building and working with startups, having been a 3x founder earlier in my career and an active angel investor along the way. Originally from Hong Kong, I began my career at McKinsey in Asia and started investing as a proprietary trader at Bank of America Merrill Lynch.

Summary:

• Zoe diet results and food obsession. 0:05
• Bethany discovered she's highly reactive to sugar through a Zoe diet test, meaning she must avoid it for the rest of her life.
• Bethany can process fats easily but struggles with sugars, including fruits like raspberries and lemons.
• Bethany struggles with an abnormal obsession with food, which has led to medical anxiety and a fear of fatty liver disease.
• She has realized that her anxiety is not related to diet but rather a combination of her upbringing, personal experiences, and a lack of understanding about preventative medicine in the UK.
• Career transitions and personal growth after recognizing mortality. 5:44
• Bethany reflects on her father's death and its impact on her perspective on life and work.
• Bethany wants to use her inherited money to pursue her passions and explore new experiences without worrying about financial constraints.
• She is considering how to use her next decade to make the most of her life and career, with a focus on fun and exploration.
• Brandon and Bethany discuss their goals and motivations, including starting a community for ambitious people and advocating for cannabis legalization in the UK.
• Bethany is taking a writing course and a pottery course to improve her skills and push herself outside of her comfort zone.
• Vulnerability, self-expression, and career growth in one's 40s. 11:57
• Bethany shares her insights on the importance of vulnerability and self-expression, citing Brene Brown's work on shame and the need to share feelings with safe people to build support.
• Clea Sham joins the conversation and adds her perspective on the value of being true to oneself, even in the face of criticism or rejection from others.
• Transitioning from operator to investor with Cleo and Speaker 3. 14:33
• Cleo is an outstanding senior woman who has held various leadership roles, including COO at a home and partner at stride.
• Speaker 3 transitioned from operator to investor due to a desire for tangible businesses and working with teams, and joined Uber as CEO to think through business drivers and prioritize resources.
• Investing background informing operations roles and vice versa. 16:54
• Speaker 3's investment background informed their operations roles, including building models and making decisions based on financial data and business drivers.
• Speaker 3's experience as an operator reinforced their investing role at Stride VC, allowing them to apply their knowledge of building businesses and assessing companies.
• Speaker 3 learned to regulate their emotions and make decisions based on data in a high-pressure environment, which helped them perform as an investor.
• Speaker 3 received feedback from their team on being too emotionless and impenetrable, which could impact their ability to connect with others.
• Leadership, teamwork, and investment strategies in the tech industry. 22:12
• Speaker 3 shared a personal experience of receiving feedback from a direct report during a one-on-one meeting, which led to a valuable learning moment for them.
• The feedback was presented in a supportive manner, with the direct report acknowledging the speaker's humanity and vulnerability, and the team having the speaker's back.
• The speaker chose to stay and lead the team through the challenging moment, ultimately resulting in the team staying at the top for over six months.
• Bethany emphasizes the importance of building trust with founders, tailoring communication styles to each founder's needs, and prioritizing their comfort level in the investment process.
• Speaker 3 highlights the people side of the VC role, including sourcing, selecting, winning, and supporting founders, and how their operational leadership experience informs their approach to these tasks.
• VC vs. CEO roles, satisfaction, and stress. 28:34
• Speaker 3 highlights the differences between operating a business and being a VC, with the former providing more tangible results and the latter offering a wider range of people to learn from.
• Speaker 3 finds personal growth and meeting new people satisfying aspects of being a VC, with the opportunity to learn from a diverse range of founders and investors.
• Speaker 3 highlights the benefits of VC, including more control over time and the satisfaction of supporting founders.
• Both identifying the next investment and making non-reversible decisions are stressful aspects of VC work.
• The challenges of time management for venture capitalists. 33:29
• Speaker 3 discusses the challenges of managing multiple boards and sourcing new investments while also prioritizing thinking time.
• Brandon adds that quality thinking is crucial to understand the legs of a product opportunity in a rapidly changing market.
• Speaker 3 describes their role as a "lone wolf" investor, responsible for researching and deciding on investments, while also being part of a team that looks at things together on designated days.
• Speaker 3 highlights the need to create time for both solitary work (developing a thesis, drilling down into an industry) and social work (meeting founders, going to events) to be successful in their role.
• Becoming an investor, including self-reflection and networking. 39:24
• Speaker 3 suggests starting small by investing with your own money and building a network of investors, founders, and operators.
• Speaker 3 advises spending time understanding the different types of VC firms and their approaches to investing, rather than rushing into a decision.
• Reflect on your energy sources and strengths to determine if investing is the right career move (42:47)
• Making a switch to investing is not irreversible, and people can switch back and forth in mature venture markets (43:53)

In this episode we discuss: "The Wartime COO”. Our special guest is Huw Slater, COO of Oliva Health, formerly COO of TravelPerk and Bella Riemer, Head of Operations at Joblift. We discuss the following with Huw and Bella: 

• What is a Wartime COO? How does this impact how you operate the business?
• How do you surface existential threats to the organisation and inject a sense of focus, without scaring folks?
• What have been some of the worst storms you’ve weathered? Lessons learned?
• More broadly, what are risks the COO should always be vigilant about? 
• What would you recommend tactically in a wartime setting? 
• How do values pragmatically inform your decision-making process in wartime? 
• Who was in your war room? Why? 

References: The Hard Thing About Hard Things

Biography: 

Huw Slater, COO and Co-founder @Oliva. With >10 years of experience in scaling tech companies in Europe, Huw Slater is the COO and co-Founder at Oliva. Prior to this, Huw was the Chief Operating Officer of TravelPerk, helped Box through their IPO by globalising their growth, scaled Typeform’s expansion from Europe to the US and drove the series B funding, and has 10 additional years’ experience as the Finance Director of a $5bn turnover division in a FTSE 10 company. A passionate leader, Huw is excited by making an impact and instilling a growth mindset in his people where transparency and clarity are key.

Bella Reimer, Operational Leader | Strategy Growth | Speaker & Mentor. With over 14 years of experience in various roles and industries. I am a passionate operational leader with a proven track record of driving efficiency, strategic growth, and cross-functional collaboration. I specialise in overseeing end-to-end processes, optimising operations, and aligning teams to achieve impactful results.

In this episode we discuss: "Efficiency Unleashed: NoCode Revolutionising Operations”. Our special guest is Philip Lakin, Co-Founder & CEO of NoCodeOps. He is the ultimate MacGyver and an ambassador for reimagining the future of internal innovation. We discuss the following with Philip: 

• What is NoCode? Why does it matter? 
• What is a tangible example of business impact? 
• Should ops professionals report into the COO or the functional lead? 
• How do you get buy-in to internal operations initiatives? 
• How do you manage dependencies and scale no-code automations? 
• What is the impact of AI on NoCode? What should we do in ops to get prepared? 

References: 

• NoCodeOps 

Biography: 

Philip Lakin is the co-founder and CEO of NoCodeOps, a community and automation management platform (Operator) dedicated to supporting operations professionals that are reimagining the future of internal innovation with no-code. He was previously the Solutions Architect for National Operations at Compass where he built the onboarding program for over 15,000 real estate agents across the United States. He has more than 8 years of experience in operations, internal system implementation, field marketing, and onboarding.

In this episode we discuss: "Surfacing the COO's Crucial Role in Revenue Generation". Our special guest is Pete Crosby a coach, lecturer & advisor, focussing on the successful design & execution of SaaS revenue & growth strategies. He is a 4x successful scale up revenue leader, most recently as CRO at Ometria.

We discuss the following with Pete: 

• What kind of focus helps enable revenue generation? 
• How should the COO’s “system thinking” be leveraged? 
• Where should revenue operations live? 
• What are the types of revenue ops leaders? How does that define their relationship with operations? 
• How important is it for the COO to have a good understanding of revenue ops? 
• What responsibility does a COO have in financial forecasting? 
• How do organisations get more commercially efficient? 
• 
  

References: 

• revenue.ghost.io (Pete’s weekly newsletter & deep dives on revenue topics each Sunday) 
• 
  

Biography: 

Pete is a coach, lecturer & advisor, focussing on the successful design & execution of SaaS revenue & growth strategies. 

He conceived, wrote & teaches The Definitive Guide to Revenue Leadership syllabus at Sales Impact Academy with Mandy Cole of Stage 2 Capital. Guest lecturers on his course include Mark Roberge, Zoom’s Greg Holmes, and Tableau’s Elissa Fink. 

He is a 4x successful scale up revenue leader, most recently as CRO at Ometria, who Deloitte placed in the Top 10 growth businesses in the UK with revenue acceleration above 3000%.  He took Ometria to its $21m Series B in just 18 months.

Prior to Ometria, Pete ran revenues at Viadeo from Series A to IPO, and took Triptease from $2m to $10m ARR and a successful Series B, also in just 18 months.

Now the Founder of Pete Crosby Revenue, he has managed revenue teams in Beijing, Singapore, Moscow, Mexico City, Dakar, Casablanca, San Francisco, Boston, New York & in most major cities across Europe.

Currently he is a board advisor to 5 of Europe’s most exciting B2B SaaS scale-ups. He also coaches revenue leaders at a further 50+ start-ups & scale-ups.

In this episode we discuss: "The COO's Endless Battle: Navigating Legal and Enterprise Contracts". Our special guest is Ahmed Badr, COO of GoCardless. Ahmed also worked for Microsoft, where he supported multi-billion pound licensing deals. 

Bethany and I discuss the following:

• The importance of a generic contract template
• Empowering sales to get contracts done
• Default and deal-breaker positions on indemnity and limitation of liability
• 
  

We discuss the following with Ahmed: 

• What did Microsoft do well and what could be reused at GoCardless? 
• What did the empowerment playbook look like with contracts? 
• What is a deal desk and how was it used? 
• What is the COO role at GoCardless? 
• When should organisations transition from outside to inhouse legal counsel?
• Why is taking a reasonable, mid-point position on default terms so important? 
• What is a sensible approach to indemnity and limitation of liability?
• What is the best way to roll out “contract empowerment” programs to sales? 
• 
  

References: 

• This guide from Deloitte
• 
  
• An article from Juro (a SaaS provider)
• 
  
• This Docusign case study on GoCardless
• 
  
• This book by Alex Hamilton (who runs Radiant Law - a legal outsourcing and automation provider)
• 
  
• 
  

Biography: 

Ahmed is Chief Operating Officer GoCardless, where he is responsible for all core operational teams, as well as being functionally responsible for legal, risk and compliance. GoCardless believes that bank payments are the best way to pay and get paid, and helps businesses collect both recurring and one-off payments, without chasing, stress or expensive fees. Before joining GoCardless, Ahmed worked for Microsoft, where he supported the multi-billion pound UK licensing and developer support organisations. Before this, he was a project finance lawyer at Allen & Overy. In 2015, he became GoCardless’ first lawyer and has since supported the business in its rapid expansion across legal, compliance, risk and operations. Ahmed also sponsors the company’s BEAM (Black, Ethnic and Asian Minority) group, and likes to use his experience to support young fast growth companies, help shape regulation, and open up access to legal careers to a wide range of individuals.