25 GTM Leaders on What’s Working and Career Learnings

We’ve got something special for you: a compilation of what is working and career learnings from some of the best go-to-market leaders out there.

Building in a silo is not only lonely; it’s slower.

Insight and perspective from others helps expedite progress.

That’s exactly what we aim to do by sharing insight through GTMnow from some of the best operators: help you build and grow faster and better, level up, and get wherever you want to go.

This is all done thanks to a give-first mentality from leaders, enabling us to bring you real, reliable and relevant go-to-market insight from from A+ operators.

This week, we’re diving into what’s working in go-to-market and some career learnings from some of the best – let’s get into it.


GTM Leader Perspectives

Highlighting 25 GTM perspectives on what is working and career advice 👇

“What’s one tactic or strategy that’s working for you?”

  • Giving customers optionality, allowing them to buy how they’re comfortable buying (Sean Marshall – former Senior Vice President of Sales at Klaviyo).
  • Private dinners (Daniel Wiener – Founder of You Should Talk To).
  • Talking to tons of people to get ahead of learning curves (Mike Vichich – former Co-Founder and CEO of Wisely, current Co-Founder and CEO of Pursuit).
  • A people-first approach to building (Sophie Buonasissi – Vice President of Marketing at GTMfund).
  • A people-driven culture: Every business is a people driven business – you need people to affect processes, to build those processes, and to upgrade and keep evolving those processes (James Isilay – CEO of Cognizant).
  • Creating more video content (Zach Lawryk – previous VP of Solutions Consulting at Slack, current head of Global Solutions Consulting at Rippling).
  • Getting leaders of different functions listening and involved (Ang McManamon – Vice President of Sales at Crunchbase).
  • A practice of gratitude (Dan Reich – Co-Founder and President of DIBS Beauty).
  • Being super smart and using data to your advantage when you prospect (Sam McKenna – Founder of SamSalesConsulting).
  • Spending time figuring out how everyone works well as an executive team (Melanie Fellay – CEO and Co-Founder of Spekit).
  • Being good at the fundamentals every single day (Eli Rubel – CEO of MatterMade and NoBoringDesign).
  • Narrow down, not being too broad (Dave Gerhardt – former Chief Brand Officer at Drift, current Founder and CEO of Exit Five).
  • Having some free version or trial (Adam Schoenfeld – Co-Founder and CEO of Keyplay and Co-Founder of PeerSignal).
  • Not doing things that don’t come from the right motive. Want to beat your competitors? Yes. But beating up your competitors? Let them beat themselves up (Elissa Fink – former Chief Marketing Officer at Tableau).
  • Being willing to co-sell (Jamal Reimer – former Commercial Vice President at Saama, current Founder of Enterprise Sellers).
  • Rehearsal journaling – it’s a form of visualization, but it’s done with a journal (Kevin Bailey – Co-Founder and CEO of Dreamfuel).
  • Running role play sessions (Dave Kennett – Founder and CEO of Replayz).
  • Getting off the high horse – if someone has a high horse. Doing the work to support, because outreach from a CEO, a C-Suite member, drives the needle way more than a seller saying, “following up again” (Cara Felleman – former Vice President of Sales at Vividly).

“If you can sum up your learnings in a few sentences today, whether it’s something we talked about today or general learnings you would want to impart in folks, what would those sentences be?”

  • Be a student of the game (Mark Cranney – former Chief Operating Officer at Skydio).
  • Growth is the only thing that matters. If you can focus on growing yourself, growing your skills, growing your toolkit – no matter where you start from, you may not be a very talented seller or customer success person, but if you’re the one that’s growing faster than people around you, you can basically overcome any single deficit (Kyle Norton – Senior Vice President of Sales and Partnerships at Owner).
  • Consistently, constantly be in learning mode because it absolutely doesn’t get easier. It only gets harder (May Habib – Co-Founder and CEO of Writer).
  • Accept not knowing perfectly what are the next 10 years going to look like (Dini Mehta – former Chief Revenue Officer of Lattice).
  • Take ownership of a business point of friction (Nicole Wojno Smith –

    Vice President of Marketing at Tackle).

  • Embrace the importance of serendipity (Suresh Khanna – former President at AdRoll Group, current President and Chief Operating Officer at Treez).
  • You don’t get promoted for doing your job really well. That’s what you’re paid for. That’s your job, that’s table stakes. If you want to get promoted, do something above and beyond. In particular, try to pick something that helps your boss (Bob Elliott – former Chief Revenue Officer at Built Technologies and Forter).

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👀 More for your eyeballs:

Adobe’s $20 billion acquisition of Figma fell through. However, even without Adobe things don’t look terrible for Figma – read more about Figma’s silver lining.

LEGO went from bankruptcy to a $11B empire – read more about LEGO’s crazy plot twist in Alex Lieberman’s article where he does a deep dive on how everything unfolded.


👂 More for your eardrums:

You’ve read perspectives of go-to-market leaders.

Now, if you want to hear them plus 25+ additional perspectives, pop in your headphones for this week’s podcast episode!

You’ll hear the the compilation of responses to the question:

What’s one tactic or strategy that’s working for you or the companies you’re serving?


🚀 Start-ups to watch: 

Dan Wright (Co-Founder and CEO of Armada / former CEO of DataRobot) and Jonathan Runyan (Co-Founder and COO) released their startup to the world last week: Armada, the world’s first full stack edge computing platform. Their mission is to bridge the digital divide and bring connectivity, compute, and AI to the most remote corners of the globe. Read more in Forbes’ article or watch the video on their website.

SALUS Technologies secures Series A funding to revolutionize construction safety software.


🔥 Hottest GTM jobs of the week:

  1. Sales Manager, Growth at Crossbeam (Remote)
  2. Enterprise Account Executive at Patch (San Francisco)
  3. Revenue Operations Analyst at SESO (Remote)
  4. Customer Success Lead at Magical (Remote)
  5. Customer Implementation Manager at Gorgias (Toronto, Canada)

See more top GTM jobs on the GTMfund Job Board.


That’s it, that’s all.

We had a blast going through the perspectives of GTM leaders to compile this list for you.

Curious what you think. Feel free to share any reactions or what’s working for you in the comments.

Wishing you all happy holidays ahead! While taking a break to enjoy quality time with family, I’ll be back in your inbox next Friday.

Spoiler alert: next week, it will be another compilation, but we’ll be spicing things up with some hot takes 🌶️

Barker ✌️

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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