Soft Sides

Laura Colagrande
  • 4.8 (9)
  • CAREERS
  • UPDATED BIWEEKLY

Welcome to Soft Sides, the show where we explore the intangible, sometimes emotional, soft sides of Go-To-Market teams. The biggest challenge for GTM leaders is not the work itself. The hardest part is building the right team, getting alignment, learning how to navigate difficult conversations, and feeling that your work matters to you and others. Our first series focuses on "influence," featuring candid conversations with CMOs, CROs, product, and partnership leaders as we break down challenges and redefine influence. New episodes are released weekly. softsides.substack.com

  1. 15H AGO

    Olga Lykova: Losing Your Best Employee (and Why That's a Sign You're Doing It Right)

    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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    49 min

  2. 17H AGO

    Jess Cook: Collaboration as a Superpower, and How to Sell Ideas That Stick

    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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    47 min

  3. 04/24/2025

    Greg Portnoy: Influence Without Authority, and How to Create GTM Alignment

    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!) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    36 min

  4. 12/18/2024

    Jill Rowley: Trust is the New Data. Selling Change, and the Evolution of Partnerships and B2B sales

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    48 min
  5. Stewart Hill House, Head of Content at Mutiny | AI and The Future of Content Marketing

    11/29/2024

    Stewart Hill House, Head of Content at Mutiny | AI and The Future of Content Marketing

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    50 min
  6. Kathleen Booth, SVP of Marketing and Growth at Pavilion: A Guide To Me

    11/13/2024

    Kathleen Booth, SVP of Marketing and Growth at Pavilion: A Guide To Me

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    41 min
  7. Jocelyn Brown, CS & Revenue Executive | From IC to People Leader, a Work In Progress Playbook

    10/20/2024

    Jocelyn Brown, CS & Revenue Executive | From IC to People Leader, a Work In Progress Playbook

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    37 min
  8. Partho Ghosh, VP of Product at Uberall: The Product-Vision Gap

    08/25/2024

    Partho Ghosh, VP of Product at Uberall: The Product-Vision Gap

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com

    43 min
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4.8
out of 5
9 Ratings

About

Welcome to Soft Sides, the show where we explore the intangible, sometimes emotional, soft sides of Go-To-Market teams. The biggest challenge for GTM leaders is not the work itself. The hardest part is building the right team, getting alignment, learning how to navigate difficult conversations, and feeling that your work matters to you and others. Our first series focuses on "influence," featuring candid conversations with CMOs, CROs, product, and partnership leaders as we break down challenges and redefine influence. New episodes are released weekly. softsides.substack.com

Information

  • Creator
    Laura Colagrande
  • Years Active
    2024 - 2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © Laura Colagrande
  • Show Website
    Soft Sides