Soft Sides

What happens when the person you’ve spent a year developing tells you they’re leaving for their dream job at Google?

For Olga, it was one of the proudest moments of her career. She had helped her regional director to grow and believe in herself in ways she never had before. And then she watched her leave.

In this conversation, we talk about how to build teams, why Olga took a seemingly smaller title for a bigger revenue challenge, and her framework for setting “North stars” and bringing focus to her team.

We also get into Olga’s path, how not getting the role she really wanted led her somewhere better, what to look for when hiring for grit and curiosity, and the best career advice she ever got: “Tell yourself you’re excited, not nervous. Your body can’t tell the difference.”

Connect with Olga Lykova: LinkedIn Connect with Laura Colagrande: LinkedIn

Timestamps:

* 00:00 Introduction

* 01:21 Leadership and team dynamics

* 06:15 Early career lessons

* 09:56 Job market and networking

* 15:56 Strategic leadership challenges

* 21:59 Acquisitions and integration

* 25:49 Working with senior leadership

* 33:13 Career transitions and impact

* 38:41 Hiring for curiosity and grit

* 45:08 Influence Shout Out and Closing

One thing you’ll take away:

The hardest part of building leaders is knowing the best ones will eventually outgrow you. The reward is they’ll still call you when they do.

Mentioned in this episode:

Kat Heisler’s episode on Rules to Thrive. Olga’s former regional director, now leading Workspace Partnerships at Google.

What does it take to go from copywriter to executive at a YC-backed company? For Jess, it started with doing it scared.

Jess spent over a decade as a creative at top agencies, writing scripts for Snap, Crackle and Pop, tweeting as Tony the Tiger, and leading campaigns for brands like Kellogg’s and McDonald’s. Then she made a pivot that terrified her — leaving advertising for B2B tech — and had to learn an entirely new way of thinking, working, and selling ideas.

In this conversation, we talk about what it actually looks like to collaborate across teams when your work depends on other people to distribute it, how to build confidence through repetition (not before it), and why the best marketing comes from understanding everyone else’s job as well as your own.

Connect with Jess Cook: LinkedIn Connect with Laura Colagrande: LinkedIn

Timestamps:

* 00:00 Intro

* 00:29 The research report “oh s**t” moment

* 04:22 How to get people to care about your work

* 07:47 From Tony the Tiger to B2B marketing

* 12:03 Learning to tie creativity to business impact

* 14:52 The “what happens if...” mindset

* 20:10 Finding the company that celebrates creative thinking

* 26:07 Why creative people will win the next wave of marketing

* 28:51 The Happy Meal box lesson (understand your job and everyone else’s)

* 33:48 How to talk about collaboration in job interviews

* 37:43 “Control the s**t out of what you can control”

* 41:15 Influence Shout Out and Closing

One thing you’ll take away:

Collaboration isn’t a soft skill — it’s the skill. The people who move up fastest are the ones who understand not just their role, but everyone else’s.

Guest: Greg Portnoy, CEO at Euler

What does it actually take to build a Go-To-Market team that is truly aligned, and why does that matter?

Greg built multi-million dollar partner ecosystems at Attentive and Hawke Media before becoming CEO and Co-Founder at Euler, an end-to-end platform to scale partner programs, accelerate revenue, and track impact.

His approach combines data-driven methodology with a deep understanding of human psychology and the incentives that drive behaviors.

In this conversation, we talk about building and scaling partnerships programs, but it's less about partnerships and more about thinking first principles and building a GTM strategy that works for your customers.

We discuss how to have difficult conversations, drive internal alignment, reflect on lessons learned (sometimes the hard way), and explore Greg's journey from partnerships leader to founder.

Connect with Greg Portnoy: LinkedIn

Connect with Laura Colagrande:LinkedIn

Timestamps:

* 00:00 Intro

* 05:31 The Importance of Alignment in Go-to-Market

* 15:27What inspired Greg to build Euler

* 19:25 Identifying Market Gaps and Customer Needs

* 21:17 Frameworks to Think about Partnerships

* 23:28 How to Become More Data Driven

* 26:24 Everything we Learned from Ryan Murden

* 29:21 Executive Alignment and Managing Up

* 31:47 Communicating Value to the C-Suite

* 35:43 Influence Without Authority: Building Relationships

* 39:00 Influence Shout Out and Closing

In this episode, we mention Ryan Murden, one of the smartest Partnerships and Revenue leaders I know (and one of the best managers I’ve ever had!)

Guest: Jill Rowley, SaaS Legend, Advisor, Board Member and so much more

What does it take to go from being one of Salesforce's first employees to becoming a trusted advisor for the industry's most innovative companies?

From shaping how enterprise software is sold at Salesforce to advising today's fastest-growing tech companies, Jill Rowley has been at the forefront of B2B. Through Eloqua's rise and Marketo's $4.7+ acquisition by Adobe, she's consistently redefined what's possible in go-to-market strategy.

In this candid conversation, Jill shares her philosophy on continuous learning, partnerships, and why trust is the new data in enterprise sales. She also opens up about burnout, the complexities of professional identity, and her evolving definition of success.

In this conversation, they explore:

* Why earning attention is harder than ever in B2B sales

* The shift from FOMO to FOMU (Fear of Messing Up) in enterprise buying

* How to sell change by painting a vision of what's possible

* Why partnerships are the next frontier of growth

* The dark side of winning and lessons from burnout

Connect with Jill Rowley: LinkedIn

Connect with Laura Colagrande:LinkedIn

Timestamps:

* 00:00 - Intro

03:19 - On Being an Underdog, Drive and Determination

07:02 - The Evolution of B2B Sales: from FOMO to Trust

14:53 - The power of partnerships

34:18 - Burnout, Trade-offs and Turning Points

43:00 - Sense of Identity and Redefining Success

43:54 - Influence Shout Out and Closing

In this episode, Jill also mentions:

* Must-Follow Partnerships Leader: Kelly Sarabyn

* Mentioned Book: The Jolt Effect by Matt Dixon

What happens when artificial intelligence becomes better at your job than you are?

Laura sits down with Stewart Hill, Head of Content at Mutiny, whose journey from AI skeptic to innovator began when he faced a stark reality we all face: automation could outperform him at writing (and many other tasks).

Now, he's testing new approaches to content creation in an AI-powered world. As someone who built his career on writing skills, Stewart shares tactical lessons learned and his vision for the future of content marketing.

In this conversation, they explore:

• Why content teams will become smaller but more impactful

  
  



• The shift from "how" to "why" in content creation

  
  



• Why tomorrow's content leaders will be more like creative directors than writers

  
  



• How to build "proprietary content formats" that AI can't replicate

  
  



• A practical framework for automating content workflows

  
  

  
  

  
  

Connect with Stewart Hillhouse

00:00 -- Intro
03:00 -- One-Person Content Team
06:13 -- Creative Campaigns: Lightning Strikes in Marketing
09:04 -- Hot Takes on Content Teams Reporting into Growth
11:55 -- Becoming More Number and Data Focused
15:16 -- Embracing AI: From Skepticism to Utilization
18:09 -- The Future of Content Creation in an AI-Driven World
25:47 -- How to Make the Most of AI
28:43 -- Rethinking all Workflows: Tactical Playbook
33:57 -- Creating Proprietary Content Formats
41:06 -- The Future of Content Creation and Distribution
42:32 -- The Importance of Taste and Creative Vision
45:14 -- Influence Shout Out and Closing

Tired of second-guessing every work interaction? From overthinking Slack messages to navigating C-suite dynamics, learning how to work with others is hard.

Laura sits down with Kathleen Booth, who found a surprisingly effective solution: she wrote an 8-page "Guide-to-Kathleen" that transformed how her teams work together. Now SVP of Marketing at Pavilion, Kathleen shares why she sends this guide to potential employers before accepting roles (and why her CEO had a similar document).

In this candid conversation, they unpack:

• Why every leader needs a "Guide-to-You"


• The "Two Ladders" framework for adaptive leadership


• Using your guide to land executive roles


• A fresh approach to performance reviews


• Why being nice isn't the same as being kind

Connect with ⁠Katheen⁠ and ⁠Laura⁠

In this episode Kathleen also mentions:

- Must-Follow GTM leader: ⁠Andrea Kayal⁠

- ⁠Radical Candor ⁠book by Kim Scott

Timestamps:

• 00:00 - Intro


• 02:56 - Day in the Life: Running Marketing at Pavilion


• 06:12 - Creating a Guide to Work with Others


• 09:01 - Managing Up and Taking Ownership


• 11:52 - The Role of Performance Reviews


• 15:05 - Understanding Task Relevant Maturity


• 18:42 - Influencing Decisions Effectively


• 24:19 - Giving and Receiving Feedback


• 30:20 - How to Improve Communication with Your Team


• 39:18 - Closing: Influence Shout-Out and Rapid Fire Questions

Guest: Jocelyn Brown, Revenue and Customer Success Leader

How do you approach the transition from individual contributor to people manager? How do great managers build trust and influence? Why is it so hard to give and receive feedback, and how do you become better at it?

Laura is joined by Jocelyn Brown, a revenue and customer success executive who has scaled teams and processes at companies like Eloqua, Oracle, and Alucadia. Jocelyn currently leads customer success and sales at Hypercontext, a B2B software company used by leaders at companies like Netflix and HubSpot to create more collaborative and productive teams.

In this episode, Laura and Jocelyn discuss:

• Maintaining focus and avoiding burnout during complex projects


• The shift in mindset needed when transitioning to a leadership role


• How great managers encourage accountability within teams


• Navigating and influencing change in complex organizations


• The idea of a "shared imagination" and why it is critical for driving team alignment

Connect with Jocelyn Brown:

• LinkedIn

Connect with Laura Colagrande:

• LinkedIn

Timestamps:

• 00:00 - Intro


• 03:17 - Navigating Loss of Vision and Finding Your Why


• 06:36 - The Importance of One-on-One Meetings


• 09:29 - Transitioning from Individual Contributor to Manager


• 12:25 - The Realities of Management as a Career Change


• 15:37 - Influence and Team Dynamics


• 18:51 - Understanding Customer Expectations and Project Management


• 22:07 - Learning from Failure and Building Trust


• 24:54 - Feedback Mechanisms in Leadership


• 27:53 - The Role of Global Experience in Leadership


• 32:25 - Closing: Influence Shout-Out and Rapid Fire Questions

Guest: Partho Ghosh, VP of Product at Uberall

Laura is joined by Partho Ghosh, VP of Product at UberAll. Partho has spent his career building products and teams at top SaaS and B2B companies, and he is known for his strategic approach to growth, product adoption, and his product philosophy centered on a build-measure-learn mindset.

In this episode, they explore what it takes to align product vision with company goals and build a culture of data-informed product teams. Partho also delves into the complexities of introducing new go-to-market motions and building relationships with marketing and sales.

They discuss:

• Driving organizational change and building momentum


• The product vision and product execution gap


• How to avoid the feature-factory trap


• Cross-functional relationships and disagreements


• Alignment and North Star metrics

Connect with Partho Ghosh

• ⁠⁠LinkedIn⁠⁠

Connect with Laura Colagrande:

• ⁠⁠⁠LinkedIn⁠⁠⁠


• ⁠⁠⁠Youtube⁠⁠⁠

Book referenced in their conversation: Inspired by Marty Cagan.

Timestamps:

• (00:00) -- Intro


• (01:19) -- Day in a Life: Running Product at Uberall


• (03:08) -- Organizational Change, Hype, and Momentum


• (04:35) -- Aligning Product Vision with Founders and Customers


• (05:05) -- How to Approach Your First 90 Days


• (08:05) -- The One Thing that All Great Product Leaders Do


• (12:01) -- Product Vision and Execution Gap


• (17:50) -- Data-Informed Decision-Making


• (22:42) -- How to Socialize a New GTM Motion


• (27:12) -- How To Deal with Defensive Colleagues


• (30:59) -- North Star Metrics and Why They Matter


• (34:59) -- How to Become a Data-Informed Product Manager


• (38:51) -- Closing: Influence Shout Out and Rapid Fire Questions

Guest: Natalie Marcotullio, Head of Growth and Operations at Navattic

Laura is joined by Natalie Marcotullio, Head of Growth and Operations at Navattic. Natalie started in B2B marketing with a focus on growth strategies like SEO and SEM, later expanding her skills in strategy and operations as a Chief of Staff. She eventually created a leadership role at the intersection of growth and marketing.

In this episode, Natalie shares how she navigates constraints at an early-stage startup and leverages community and word of mouth to drive growth.

They discuss:

• Aligning your role with business needs


• Key questions to ask when interviewing for your next role


• The "White Sneaker Theory" and community building


• How to “soft pitch” an idea and drive influence


• Building strong relationships with sales and CX teams

Connect with Natalie Marcotullio

• ⁠⁠⁠LinkedIn⁠⁠⁠

Connect with Laura Colagrande:

• ⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠


• ⁠⁠⁠⁠Youtube⁠⁠⁠⁠

Book referenced in their conversation: The Four Tendencies by Gretchen Rubin

Timestamps:

(00:00) -- Intro
(01:48) -- Transitioning Roles: From Marketing to Growth
(03:40) -- Shaping Your Role and Building Influence
(11:22) -- Changing How People Think and Act Through Marketing
(19:02) -- Incremental Steps and Realistic Expectations
(19:56) -- How to Build Community
(21:50) -- How to Build Trust with Your Sales Team
(26:03) -- The Importance of Constant Feedback Loops
(34:26) -- How to Handle Rejection and Different Opinions
(36:39) -- How to Soft Pitch an Idea
(40:56) -- Closing: The Best Marketing Advice

Guest: Arthur Castillo, Director of Content, Community & Partnerships

Laura is joined by Arthur Castillo, the Director of Content, Community, and Partnership at Aligned. Arthur started his career in sales and always had an affinity for storytelling and community. By leaning into his strengths, he crafted his own role at the intersection of community, evangelism, and sales.

In this episode, Laura and Arthur discuss Arthur's unique journey across different go-to-market roles and the lessons he's learned along the way. They delve into the importance of curiosity, adaptability, and how crucial it is to handle ambiguity when working at an early-stage startup. They discuss:

• Navigating career growth and understanding the different GTM functions


• The concept of skill stacking


• Building influence and trust within teams and across departments


• How to prepare for and run your one-on-one meetings with C-level executives

Connect with Arthur Castillo

• ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

Connect with Laura Colagrande:

• ⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠


• ⁠⁠⁠⁠⁠⁠Youtube⁠⁠⁠⁠

Arthur also gives a shout out to: ⁠Vivek Nanda⁠, ⁠Kyle Asay⁠, ⁠Obaid Durrani⁠, ⁠Todd Clouser⁠

Timestamps

(00:00) -- Intro
(03:13) -- Day in a Life: Running Content and Community
(04:31) -- Wearing Multiple Hats
(05:51) -- The Benefits of a Go-to-Market Tour
(09:43) -- The Concept of Skill Stack for Career Growth
(13:53) -- The Invisible Necklace Framework
(18:31) -- The Power of Combining Unique Experiences and Skills
(28:08) -- Seeking to Understand Before Being Understood
(30:19) -- Dealing with Ambiguity and Pivots
(37:56) -- How to Run One-on-One Meetings with C-Level Executives
(45:40) -- Closing and Influence Shout Out