The Get: Finding And Keeping The Best Marketing Leaders in B2B SaaS

On today’s episode, Erica talks with Gary Survis, an Operating Partner with Insight Partners. Erica and Gary discuss how the strongest CMOs limit risk when transitioning into new marketing leadership roles:

• They stand out by demonstrating credibility, collaboration, and curiosity. They're aware that what you don't say in an interview is just as important as what you do say.
• When interviewing, they communicate their experience with this structure: strategy + example + numbers. 
• Once in the new CMO role, they realize that no matter what their background is, they have to deliver on their demand gen goals or risk losing their job.
• They have a perspective on AI and know how they will organize their teams and define roles differently for AI-supported marketing. 
• They create a "flywheel of credibility."
• They take the time they need to form an assessment – "it'll be the only time in your tenure when you are afforded the luxury of time."
• They follow the "Diagnose, Don't Delude" approach – identifying and surfacing problems rather than sweeping problems under the rug.
• They swiftly make the org changes they need to make: "If you are not successful because the people below you are not strong, you have no one to blame but yourself for not making the changes you know you need to make."

00:00 Welcome to The Get: Season Overview

00:47 Introducing Gary Survis: Insights from an Operating Partner

01:37 De-risking the CMO Hiring Process

02:10 Common Pitfalls in Recruiting Marketing Leaders

05:01 Balancing Strategy and Execution in Marketing

11:00 Key Traits of Successful Marketing Leaders

13:19 The Importance of Curiosity in Leadership

17:15 AI in Marketing: What to Look for in a CMO

19:36 Early Steps for a New CMO

21:41 The Role of AI in Organizational Structure

22:34 Setting and Achieving Goals

24:25 Challenges in Coaching CMOs

26:53 Reflections on Past Marketing Roles

28:56 Marketing Under the CRO: A Controversial Trend

31:13 Conclusion and Final Thoughts

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

In this episode of The Get, host Erica Seidel discusses the intricacies and challenges of hiring CMOs in B2B SaaS companies. She highlights why the CMO role is particularly tough to fill, the high stakes involved, and the common concerns among CEOs and investors. 

Erica is joined by Peter Mahoney, Chief Commercial Officer at GoTo and author of The Next CMO. Peter has been a GM, CMO, CEO, and now at GoTo has recently transitioned from CMO to Chief Commercial Officer. He offers practical advice on organizational structure, fostering CEO-CMO trust, and managing expectations.

You’ll learn about:

• The complexities and fears that CEOs face when hiring CMOs
• Distinctions between roles such as Chief Commercial Officer and Chief Revenue Officer
• How "everyone at the C-level thinks they understand marketing but at the same time fears that they don't understand it"
• The skills required to succeed in a small versus a big company as a CMO
• The wisdom of spending some of your career outside of marketing…. even if it is a sideways move  
• Strategies for candidates to effectively communicate their impact during the hiring process
• Advice for rising CMOs

00:00 Introduction: The Hardest C-Level Role to Hire

00:41 Welcome to The Get: Reducing Risk in CMO Recruitment

01:14 Meet Peter Mahoney: A Journey from CMO to CCO

01:59 Understanding the Chief Commercial Officer Role

06:20 The Fears and Risks in Hiring a CMO

10:01 The Perfect Fit: Balancing Experience and Potential

13:19 Stage Experience: Scaling Up and Complexity

16:33 Embracing Flexibility and Depth in Marketing Roles

17:10 Navigating Revenue and Complexity in Marketing

17:57 Understanding Marketing Maturity and Budget Constraints

19:15 The Evolving Technical Landscape of Marketing

20:03 Effective Leadership and Strategy Alignment

23:17 Addressing CMO Candidate Concerns

24:41 Key Interview Insights for CMO Candidates

27:34 Advice for Aspiring CMOs

30:01 Career Growth and Risk Management

32:24 Conclusion and Final Thoughts

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

In this episode of The Get, host Erica Seidel explores the theme of managing risk in CMO recruitment, specifically cautioning against over-relying on a candidate's experience with a particular scale journey. Erica discusses the potential misconceptions and pitfalls when hiring marketing leaders based on their previous successes in scaling companies. 

While such experience can be beneficial, she warns that it doesn't necessarily guarantee the same outcome in different contexts. Listeners are encouraged to delve deeper into how these candidates contributed to their past successes. The episode underscores the importance of aligning expectations and understanding the nuances of each candidate's experience for a better hiring decision.

00:00 Welcome to The Get

00:16 Listener Feedback and Mid-Season Break

00:34 The Risk of Trusting Scale Journeys

01:25 Benefits of Scale Experience

02:26 Potential Pitfalls of Scale Experience

03:40 Conclusion and Final Thoughts

04:02 About The Get and Erica Seidel

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

A good leader evolves over time. A CMO’s perspective will shift as they go from first-time CMO to repeat CMO, or to CRO or CEO. As they build experience, they are able to sidestep common pitfalls and react more efficiently to new challenges. At the same time, their perception of risk in a role evolves as they get more exposure. There's an 'arc of caution' that CMOs often go through, from being open-minded early on in their careers, to being able to recognize risky situations once they have more marketing leadership experience, to being more risk-averse and attuned to the 'warts' of a role once they have significantly more experience than other marketing leaders.

In this episode of The Get, host Erica Seidel discusses the complexities of hiring CMOs in B2B SaaS companies. The conversation explores the importance of the right type of marketing leader for different phases of a company's evolution, the vital role of clear communication between CEOs and CMOs, and how CMOs can balance producing value in year 1 with delivering longer-term value beyond year one.

She is joined by Norman Guadagno, a seasoned CMO who has led marketing at Mimecast, Acoustic, and Carbonite, and who shares his experience as a CMO and CEO. Norman illustrates how experience as a marketing leader shapes a CMO's risk awareness and decision-making process.

You'll learn about:

• The 'arc of caution' in career progression
• Interaction between CMOs and CEOs - the role of a CMO can significantly vary depending on the company's stage of growth and the right marketing leader at one stage may not be the right one at a different stage
• How to embrace the duality of delivering on short-term demand capture with longer-term brand building, and how to set expectations for longer-term impacts with the CEO and other C-suite leaders
• How 50% of the CMO role has nothing to do with marketing
• Managing timeframes - first-time CMOs may be overly optimistic about how long it takes to implement change, while seasoned CMOs understand realistic timeframes for results
• Evolving dynamics in the C-Suite - "not every company needs a CMO"
• How sometimes less is more with interview questions - start simple and give the candidate room to expand on what’s important to them

This episode provides valuable insights for both CMOs and CEOs seeking to make informed hiring decisions.

00:00 Introduction to The Get

00:16 The Journey from CMO to CEO

01:14 Introducing Norman Guadagno

02:13 Advice for Aspiring CMOs

04:43 Navigating Company Culture and Change

05:21 The Dynamics of Executive Change

13:51 Balancing Short-Term and Long-Term Goals

22:07 The Role of the CMO in Business Strategy

25:33 Embracing Unique Skills and Roles

26:19 Ego and Humility in Career Progression

27:25 The CEO's Perspective on Hiring a CMO

31:00 Demonstrating Commitment to Marketing

35:25 Navigating Career Trauma and Transparency

40:49 Insights on Interviewing and Hiring

45:51 Final Thoughts and Reflections

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

In this episode of The Get, host Erica Seidel explores the crucial role of decision-making in CMO recruiting. Erica shares common traps in decision-making, such as over-trusting someone else's due diligence, over-estimating an appetite for transformation, falling in love with someone's former company without looking at their specific contribution to it, and falling prey to confirmation bias, to name a few. She shares tips for making strong, informed hiring and career decisions. 

The episode includes a deep dive with guest Melissa Sargeant, a seasoned CMO, on her experiences and strategies for doing due diligence and reducing risk when hiring and getting hired. This episode is loaded with practical advice for both hiring managers and candidates looking to make better career decisions.

00:00 The Three Pillars of a Successful Career

00:20 Welcome to The Get!

00:44 Understanding Decision-Making in Recruiting

01:48 Common Flaws in Decision-Making

04:44 Introducing Melissa Sargeant: Insights from a Seasoned CMO

05:20 Melissa Sargeant on Reducing Risk in the Recruiting Process

07:11 Maybe the company used to have product market fit, but now it doesn't

9:16 Doing mutual due diligence

12:14 The 2 key questions to ask in an interview to suss out organizational dynamics

19:15 'Your gut is your truth' and other ways to suss out red flags

25:06 Building Trust and Transparency as a New CMO… and avoiding making decisions for 30 days

25:30  'CMO roles are really revenue rescue missions'

33:29 Final Thoughts and Key Takeaways

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

The best CEO/CMO matches are ones where, BEFORE day 1, both sides collaboratively, intentionally, and explicitly surface the challenges they will face together and how they will overcome them together. That's not as easy as it sounds, though! 

In this episode of The Get, host Erica Seidel dives into the complexities of hiring CMOs in B2B SaaS companies. Drawing from her 13 years of experience in recruiting marketing leaders, Erica discusses the high risks and challenges faced by CEOs and investors during this process. 

She is joined by James Lamberti, head of go-to-market for Georgian, who shares his extensive experience in hiring and getting hired as a CMO. 

You'll learn about:

• A method for collaborative de-risking between the CEO and CMO 
• How one of the most important functions of the interview is to sketch out the company's GTM framework and identify any misalignment in GTM strategy.… because the more the company is clear on their GTM strategy, the more effective the CMO will be
• How to diagnose in the interview process when product-market fit is loosely held or when the market is defined too broadly
• The 'homework' that top CMO candidates will do ahead of their first meeting with a CEO, including defining their 'Ideal CEO Profile' and how to add value to that person
• How to identify and skirt typical threats to marketing being successful, including 'silver bullet expectations,' 'new day/new strategy' situations, under or over-hiring for the stage, and mis-selling the CMO opportunity
• What CEOs are likely to ask CMO candidates about AI

This episode is packed with valuable insights for both hiring leaders and candidates looking to navigate the high-stakes world of CMO recruitment.

00:00 Introduction: The Challenge of Hiring a CMO

01:20 Understanding the Risks in Hiring a CMO

03:25 Tips for CEOs and Investors on Hiring a CMO

04:50 Guest Introduction: James Lamberti

06:22 James Lamberti's Framework for Diagnosing a Role

17:25 Balancing Efficiency and Thoroughness in Interviews

22:57 The Importance of Customer Love and Rev Ops

25:53 Challenges and Red Flags in the Hiring Process

30:33 The Role of AI in Marketing Leadership

33:21 Favorite Interview Questions for Marketing Leaders

35:53 Conclusion and Next Episode Teaser

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

In this episode of The Get, host Erica Seidel delves into what it takes to excel at networking and effectively work with recruiters, exploring programmatic ways to engage with professional networks. Erica discusses the best questions candidates ask recruiters and the importance of developing a personal Board of Advisors. She also explains the role of executive search professionals, differentiating them from career coaches and therapists.

Special guest Tracy Eiler, CMO of OpenSesame, discusses her recent experience evaluating marketing leadership opportunities, how today's recruiting climate is unique, the fast-paced pressure-testing playbook she uses to assess roles, and red flags to watch out for. Tracy shares how CEOs can demonstrate their support for marketing, tips for collaborating with recruiters, and how CMO candidates can make a strong impression. The discussion extends to the complexities of career trauma, confidence, and the right level of transparency when delivering your 'career story.' Tracy also emphasizes continuous relationship building within one's network and the importance of having a well-prepared personal narrative.

00:00 Introduction to Networking and Recruiters

00:35 Welcome to The Get with Erica Seidel

01:06 Tips for Working with Executive Recruiters

04:09 Introducing Tracy Eiler

05:02 Tracy Eiler's Journey and Insights

08:57 Pressure Testing a Role

12:47 Evaluating CEOs and Red Flags

17:53 Tracy's First CMO Job and Lessons Learned

20:54 Collaborating with Recruiters

22:24 Navigating Recruiter Relationships

22:50 The Role of Feedback in Shaping Searches

26:24 The Importance of Networking

30:10 Building and Maintaining Meaningful Connections

33:25 Career Trauma and Vulnerability

38:01 Final Thoughts and Key Takeaways

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

Welcome back to The Get! It's Season 6 and the theme this season is 'The Race to Reduce Risk in CMO Recruiting.' We look at risk from the perspective of hiring and the perspective of getting hired.

In this first episode, host Erica Seidel shares:

• How CMO candidates can find out what they need to find out BEFORE saying yes so they can move forward wholeheartedly
• How to make efficient use of interviews despite time and access being limited
• The top questions CMO candidates ask, from culture and cap tables to
• What the best CMO candidates do during the recruiting process (not just during interviews, but more broadly) to show up as peers, demonstrate their 'altitude,' surface important insights, and mitigate risk

The episode includes a deep dive with guest Andrea Kayal, CRO at Help Scout and former CMO.

Andrea and Erica discuss:

• When it makes sense for a marketing leader to report to a CRO rather than the CEO… and why CMOs can make great CROs
• The key questions Andrea asks when evaluating a role
• Key metrics that Andrea recommends looking at to evaluate the health of the business
• How to balance efficiency and thoroughness when vetting a role
• The all-important piece of vetting cultural fit

You can read Andrea’s article on interviewing companies here.

00:00 Introduction: The CMO Dilemma

00:42 The Importance of Mitigating Risk

01:23 What Top CMOs Look for Before Saying Yes

02:54 Key Questions CMO Candidates Should Ask

04:02 Beyond Questions: Actions of Top CMO Candidates

06:14 Introducing Andrea Kayal: Insights from a CMO and CRO

08:10 Evaluating the Role of CROs and CMOs

13:27 Top Criteria for CMOs Before Accepting a Role

23:58 Final Thoughts and Conclusion

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is The Race to Reduce Risk in CMO Recruiting. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by the team at Simpler Media Productions.

Erica Seidel, the host of The Get, provides an overview of the key themes from this season. Erica runs The Connective Good, the executive search practice that specializes in placing CMOs and VPs of Marketing for B2B SaaS companies. She is known for recruiting the ‘make money’ type of marketing leaders, not the ‘make it pretty’ ones. 

This episode serves as an executive summary of the learnings from our fifth season, which has focused on the CMO and Board relationship. 

We cover:

• What do Board members want in a SaaS CMO? And how can you ace your interview with a Board member?
• Board meetings: How can you land on your feet once you are inside the Boardroom? 
• How do you build a strong dialogue with the Board OUTSIDE of Board meetings? 
• Serving on Boards: How can you become the CMO who gets tapped for Board seats? 

I designed this season to be a guide for how to upgrade from one-way reporting to the Board to a two-way dialogue. With that ongoing dialogue and collaboration, both in and out of the Boardroom, both sides will learn more, and the business is more likely to be successful. 

A huge thank you to the guests this season, who ranged from B2B SaaS marketing leaders, CMOs who have become Board members, and Board members/investors who are involved in hiring CMOs:

• Elana Anderson
• Kelly Ford Buckley
• Allison Dancy
• Evan DeCorte
• Jennifer Pockell Dimas
• Chris Fountain
• Sandra Lopez
• Madeline O’Phelan

Please tune in to each of their episodes. And, check out the episodes from the previous four seasons. Last season, for instance, we covered ‘Solving for the Scale Journey in B2B SaaS.’ 

To stay in the know for our next season, please keep following the show in your preferred podcast listening app.

Key Links

https://www.linkedin.com/in/ericaseidel/

https://theconnectivegood.com/

https://thegetpodcast.com/

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The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is the CMO and Board Relationship in B2B SaaS: How can that relationship go from fraught to functional and even to fantastic?

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by Evo Terra and Simpler Media Productions.

Sandra Lopez is a marketing dynamo who has been in marketing leadership and general management roles in many of the world's biggest and most influential tech companies, like Adobe, Intel, and Microsoft. She recently served as co-chair for the World Economic Forum for Augmented Reality and Virtual Reality. She also serves on the Board of Directors for Junior Achievement USA and PureRED, she's an advisor for Cabra Sports, and she is the co-chair for Sports Integrity Global Alliance.

We discuss:

• How to translate marketing-speak into language that CFOs and Board members can understand
• How to work with Board members who think they know more about marketing than they actually do
• How to manage expectations with Boards about how long things take in marketing and educate along the way, understanding that "it's hard to educate someone in 30 minutes"
• How to prepare for Board service – and knowing when to say no to a Board opportunity
• How interviewing for a Board seat is different from interviewing for a CMO spot

Key Links

https://www.linkedin.com/in/lopezsandra/

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The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is the CMO and Board Relationship in B2B SaaS. 

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS. 

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety - rather than the ‘make it pretty’ variety, contact Erica at [email protected]. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com. 

The Get is produced by Evo Terra and Simpler Media Productions.