Lessons Learned, Experience Gained: Ruminations on Mark Small’s Journey from Salesperson to Sales Leader

Jason Malki
SuperWarm
Published in
4 min readAug 21, 2023

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I had the pleasure of interviewing Mark Small, a global sales and revenue operations leader who has now taken on the role of Growth and Go-to-Market (GTM) Advisor to investors and startups.

Mark brings a wealth of experience and a global perspective as a senior sales and revenue operations leader to his role as a Strategic Advisor to emerging, potentially disruptive companies. He assists startups in achieving repeatable growth and scalability, leveraging his extensive background in leading global organizations for renowned SaaS and cybersecurity companies including Oracle, McAfee, Proofpoint, and Cofense. Mark’s expertise spans incubation, early-stage, and emerging growth companies, and his guidance helps founders, investors, sales leaders, and CEOs establish successful go-to-market strategies and build motivated, high-performing teams.

How did you break into your tech career?

Well, it was a little accidental, or certainly not intentional. Soon after graduating from college, I answered a help-wanted ad for Lexis/Nexis. I was still contemplating applying for law school, and I saw this as an opportunity to learn more about the legal business, sales, and with the territory covering the entire West, I’d get to travel to nice places as a bonus.

Lexis was an early application of full-text boolean search logic. It was revolutionary and completely disrupted the way legal research was done. Within a short time, we had all of the top 100 law firms as customers. That’s where I first fell in love with technology, particularly when it disrupts the status quo by offering something an order of magnitude better. It’s also where I started in sales and honed my craft while selling a highly differentiated offering.

I decided I could have more fun, and potentially make more money in sales than in law, so no law school for me and no regrets. It seems the world has done just fine with one less lawyer in the mix.

What excites you about what you’re building in your current role?

Recently, I relaunched my Strategic Advisory consultancy, MMC Ventures. I’m using my experience and expertise as an operator, specifically as a CRO/Global VP of Sales, to help start-ups, founders, business owners, and investors define, strategize, and execute their growth and go-to-market plans.

I’m not a product inventor. But once your “invention” achieves product-market fit, there’s still the huge challenge of developing your sales channels to achieve sustainable growth and scale. For founders, the shift in focus from product to sales can be profoundly challenging. Having help and expertise in dealing with the myriad of go-to-market dependencies that are the building blocks of their growth can be a huge positive. There’s a lot to get right: Demand Gen, Inbound, Outbound, website, PLG, Sales, CRM, Pricing, Bundling, Messaging, and a whole bunch of other things that come into play.

So, I’m excited to help founders and their companies through their sales and operations journey. I want to make sure that the reason for a great invention or product failing is not due to neglecting to develop the processes and people needed for effective go-to-market execution.

What has been your biggest challenge in your current role?

Setting realistic expectations. Timing matters and there are things outside the control of sales and go-to-market. Sales leaders are not magicians. If you don’t have a competitive product or an addressable market, then your primary obstacle to success is one of product and/or market. No amount of go-to-market execution and sales resources will likely overcome that.

If you had to share “words of wisdom” with a Tech Executive who’s starting their career, what would they be?

I have many, but I’ll share three now:

  1. If you want to be a great leader, there are no cheat codes or shortcuts. Remain humble, curious, and treat people as people. Think about great managers and leaders you’ve worked for or admired from a distance. They created high-performing teams and cultures. They inspired and motivated, cultivated innovation and creativity. They demanded teamwork and held everyone, including themselves, accountable. Emulate them.
  2. Data-driven is all the rage and rightly so. Defined processes reduce friction and a well-instrumented CRM is a powerful tool. But if you want to drive better outcomes, it’s wise to remember that leading is a human endeavor. There’s no substitute for connecting, engaging, and seeking to understand your customers, prospects, your team, and fellow employees. Shut the laptop and get involved in the real world.
  3. Lead from the front, or even better, beside. Never from the back. Never ask someone to do a job you yourself wouldn’t do. Remember the saying, “With power comes responsibility. With great power comes great responsibility.”

How can our readers follow you on social media?

linkedin.com/in/marksmall262

This was very insightful. Thank you so much for joining us!

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Jason Malki
SuperWarm

Jason Malki is the Founder & CEO of SuperWarm AI + StrtupBoost, a 30K+ member startup ecosystem + agency that helps across fundraising, marketing, and design.