Building GTM Flywheels with Kevin Hamilton

At Tidemark’s 2025 VSaaS Collective Live, Kevin Hamilton walked through the GTM framework he's deployed at CEB, Opower, Benefitfocus, and Toast — four companies with dramatically different markets, buyer motions, and sales cycles.

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His core argument: tactics age fast, but a good operating system compounds. What works isn't the channel of the moment. It's treating go-to-market like an operating system that can survive different markets, different cycles, and different teams. Here’s the 4-step strategy he shared: 

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Build from market truth, not marketing trends

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The foundation isn't your product roadmap or your competitor's playbook — it's a clear-eyed view of your actual market. To build a well-oiled GTM machine, you need to understand the market and buying journey better than your competition. 

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Hamilton's first move at every company: commission an annual market study covering TAM, segmentation, decision timing, and buyer journey. Not for the board deck. For operational planning.

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Two components matter most: how frequently buyers buy and the channels they actually use. At Opower, developing a framework that allowed the sales and marketing teams to accurately target which utilities were most likely in a buying cycle helped pave the way to a successful IPO in 2014.  At Toast, developing a deep understanding of decision frequency and discovery channels allowed the team to build an inbound funnel powered by organic search and referrals as the business scaled to north of $2B in ARR.   

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Force sales and marketing to run one operating system

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Once you have a firm understanding of your market, you need to drive alignment through your operating system. However, in most organizations, marketing optimizes for leads, sales optimizes for deals, and the handoff is where momentum dies. Far too often, Sales & Marketing teams are not aligned. 

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You need to build a GTM operating system and culture that is hyper-focused on alignment, testing, and optimization. In practice this looks like: weekly funnel reviews focused on pacing versus plan and “red-to-green” accountability, marketing variable comp tied to bookings rather than MQLs, and SDR resourcing focused on input metrics (over output). Kevin shared how at Toast, marketing channel leaders felt accountable for bookings targets, worked closely with sales leadership, and would run time bound sprints when funnel volume was behind plan.

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For small TAM or enterprise models, the operating system looks different. At Opower, the GTM team employed a "rifle model"—every account in a spreadsheet, enriched with purchase signals (regulatory approvals, energy efficiency mandates, cost per kilowatt hour). Accounts tiered high-medium-low. Clear ownership split between sales and marketing. Weekly pipeline reviews tracking movement against those tiers. The operating system matched the motion: focused, account-based, measured.

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(For more on how to build high-performing sales and marketing teams, check out Kevin’s piece here.) 

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Invest in the next frontier

Market surveys reveal the discovery channels where buyers actually make decisions. Then you allocate accordingly.

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Once you build rigor around your TAM and get your operating system running smoothly, you can start allocating GTM investments that maximize long term decision penetration. Still, don’t lose sight of your buyer and their journey. At Toast, this looked like building a strong organic funnel through investments in brand and community.

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Drive productivity through focus, not expansion

Lastly, the instinct when growing is to give reps bigger territories. Hamilton proved the opposite works better.

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As Toast grew its footprint, they didn’t respond by carving bigger and bigger territories. They did the opposite. They shrank territories, added enablement, and increased specialization. Cutting territory size by roughly a quarter actually pushed productivity up for fully ramped reps. Focus, he argued, is the only real accelerant.

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The framework that compounds

Four companies. Four different markets and sales motions. One message: know your market cold, run a single operating cadence, and let actual buying behavior dictate your tactics. 

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Do those things consistently and the flywheel shows up. This framework isn't a quick win. It's a system built to compound — one that survives different teams, different markets, and different cycles. 

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Strategy first. Tactics second.