Our sales team has just come off a transformative 2025, and we’ve come away with our fair share of hard-earned insights from this past year (or, to be frank, since 2023 – a tough year that required us to make meaningful progress every quarter since, and one that gave me a heart condition for the rest of my life!). 

As we dive headlong into 2026, everyone is trying to find the next hot thing that’ll drive big wins in their GTM playbook. For my part, I recommend a return to the fundamentals of GTM – things like Ideal Customer Profile, retention strategies, partnerships, innovation and team culture – to build a winning GTM strategy for the year ahead.

Here are six key lessons we learned the hard way in 2025, which I hope will spark ideas for your own GTM playbooks:

In 2025, one lesson rang loud and clear: Doubling down on the right customer segment drives sustainable growth. For us, that meant a major push into the mid-market. By year’s end, these customers accounted for 45% of our customer base but 66% of our ARR. 

Why? Mid-market means momentum: They have more complex integrations and stick around because of the trust you build with their teams. And, because they spend more, you can spend time with them! 

What’s more, these customers delivered far higher retention and expansion rates (with an NRR well above 100%, vs. an abysmal 70–80% for micro-SMB customers). Yes, bigger customers have bigger needs, but they pay off in larger contracts and longer relationships.

Average deal sizes also climbed as we moved up-market, and multi-year contracts became the norm, validating that we’re delivering long-term value. By Q4, 74% of newly signed ARR was in 2-year+ contracts, a strong sign of customer confidence and product-market fit. 

Simply put: when properly served, bigger customers create a more durable revenue base. They churn less and expand more, fueling a healthier business.

Takeaway for 2026: Narrow your ICP, targeting the segments where you can win and grow the most.

Another 2025 lesson: GTM fundamentals and disciplined execution matter – a lot.

Early in the year, we tightened our sales and marketing process, and it paid off in spades. Pipeline quality improved even as we grew volume, and sales efficiency climbed sharply. By Q4, our sales team had achieved an all-time high ARR per rep — with some reps selling multiple $100K new business months in a row — and consecutive 100%+ quota attainment quarters. In fact, Q4 was our largest net-new ARR quarter ever. 

This wasn’t luck. It was the result of rigorous deal execution and a focus on the highest-value opportunities. When we stuck to a defined process and qualified hard, we closed more and better deals.

One pain point we uncovered was a lack of big-fish prospects entering our funnel. Only ~10% of inbound opportunities in 2025 were with companies with larger sales teams. This meant that we were under-engaged at the upper end of our mid-market ICP. 

The fix? Don’t wait for enterprise leads to fall from the sky; go out and get them. 

We’ve since stood up an outbound function dedicated to targeting larger mid-market accounts and, in 2026, we’ll be doubling down on industry events (e.g., conferences, summits, community meetups) that put us in the same room as CFOs and sales leaders of bigger orgs.

We’re anticipating longer sales cycles, multi-threaded conversations, ROI justification, and engaging CFOs early are all critical. (In 2025, whenever we involved finance executives too late, our win rate in deals led by CFO evaluations lagged). 

Going forward, we’re upskilling the team to sell more complex deals, with focused training on value articulation. At the same time, we’re being more proactive about pipeline generation. The rewards of this discipline are very real in the form of bigger quarters and fatter pipelines.

Takeaway for 2026: Efficient GTM teams balance rigorous execution with the flexibility and know-how to meet customers where they are.

If 2025 taught us anything, it’s that the real victory isn’t just winning new deals; it’s keeping and growing them. 

We saw a clear divergence in customer health between those we retained and those we lost. NRR became our North Star metric, and improving it required a mindset shift: Play the long game with customers from Day One. Concretely, that meant selling multi-year agreements and investing in customer success early. The result: By year-end 2025, 80% of new business ARR was signed in multi-year deals, and most of our renewing ARR was locked into 2-year+ contracts. Pushing for longer-term commitments not only provides greater revenue visibility but also forces both customers and us to truly commit to the partnership and value delivery over time.

Historically, we relied on heroic efforts late in the customer lifecycle to save at-risk accounts or to land upsells. But that approach doesn’t scale. And so, in 2025, we embedded our Account Managers (AMs) and Solutions team earlier in the customer journey to ensure each customer saw value faster and more consistently. The impact was immediate; we beat our upsell plan in the second half of 2025 and drove NRR well above 100%. In fact, when we placed AMs at the start of onboarding, expansions started happening earlier in the lifecycle. By mid-year, we’d doubled the rate of multi-year renewal signings. 

We’ve also renewed our focus on time-to-value: The sooner a customer sees tangible value, the better our chances of keeping them. In practice, this meant streamlining onboarding, providing robust enablement (online academies, admin training), and using data to drive engagement. And, we identified signals to proactively reach out when an account was ripe for upsell or at risk. 

Takeaway for 2026: Customers are an integral part of the GTM engine, and long-term customer value should trump short-term sales whims every time.

Customers want a solution that fits in an aligned methodology, and they don’t care where it comes from. 

When you align with other platforms and/or partners that serve your target market, 1 + 1 can equal 3, and it can supercharge your distribution efforts. 

A stand-out example: Our integration and co-selling partnership with HubSpot delivered 70% ARR growth YoY. Not only did the volume of deals rise but, because HubSpot was aligned to our upmarket mission, the deals got bigger and our win rate improved over 50% YoY!  

We saw a similar boost after launching a new integration between payroll and the HRIS. In less than a year, the integration contributed more than 20% of new ARR, with those attached deals carrying a higher ACV to boot. Even better, customers who used our product alongside Rippling derived greater value and stayed longer.

For our sales team, having a trusted partner’s endorsement (and a seamless tech integration) made our product an easier sell. The lesson: integration partnerships can dramatically increase deal size, win rates, and retention when the partner’s product complements ours.

One caveat: Not every partnership will bear fruit, and we learned the hard way to pivot away from those that don’t. Early in 2025, we invested in solution-partner channels that fizzled out, and so, we reallocated those resources to where we saw traction: core tech partners. In 2026, we’re doubling down on an ecosystem-based GTM approach.

Takeaway for 2026: Partnerships are a force multiplier for sales and distribution, extending your reach, lending credibility, and even directly funneling opportunities your way. When looking for the right partnership opportunities, ask: who already has trust and distribution with the customers we want, and how can we team up with them?

(Honestly, aren’t we all saying to ourselves, “there are too many buzzwords, too much noise here”? This lesson is for those of us who are overwhelmed and don’t know where to begin.) 

For us, building a winning GTM strategy is about learning what was practical and what was not, and applying those learnings moving forward. 

Which leads us to an insight that took us by surprise in 2025: a not-insignificant amount of demo’ed pipeline in 2025 came from ChatGPT. 

Yes, you read that right! 

By getting creative with GEO for prospect outreach and content, we identified real opportunities that led to product demos. This was part of an experimental “GEO program,” where we used AI to craft tailored messages and identify leads. The results were eye-opening: AI can augment top-of-funnel activities; it can research accounts, personalize emails at scale, and even engage visitors through chat, essentially doing some of the work of an SDR, but faster and at a fraction of the cost. If 6% of pipeline can come from a few early AI experiments, we’re eager to see what a fully operationalized AI-assisted outbound motion can do in 2026.

When you free up human sellers for the relationship and strategy work, and let algorithms handle the grunt work and pattern recognition, you’re not only increasing productivity. You’re also opening the door for further innovation – not to mention, new partnership opportunities – that can help to shape your GTM playbook moving forward. 

Takeaway for 2026: Sales teams that embrace data and AI will be faster, smarter, and more scalable, essential traits as we face bigger targets in coming months.

Amidst all the strategy shifts and new tactics, one of our most pivotal lessons of 2025 was the power of an aligned, motivated, and well-incentivized team.

We made a concerted effort in 2025 to improve team culture, communication, and morale, and the results were tangible: Our Employee Engagement Scores (eNPS) skyrocketed by +35 points. This wasn’t a random uptick; it correlated with intentional changes we implemented: 

In practice, we overhauled how we run our teams, adding more transparent goal-setting and quick action on feedback. Each department knew how its work tied into the bigger picture. And when people see their impact, they step up. 

By year’s end, the buzz within the sales org was palpable; we had momentum and confidence heading into 2026. 

While not everyone’s a fan of eNPS, I’d suggest that, at minimum, you have an “early indicator” of what might not be working with your people, and double down on the things that are!

(Why am I highlighting this “soft” stuff in a sales strategy article? Because culture proved to be a secret GTM weapon. Quite simply: A happier, engaged and incentivized team that understands company objectives performs better.)

In 2026, we’re not taking our foot off the culture pedal. We’re reinforcing alignment and purpose with an in-person, company-wide kickoff in San Diego at the start of the year. Managers are being trained to lead through the next phase of growth, ensuring we preserve that tight coordination even as we scale. 

Takeaway for 2026: Treat your team culture as seriously as your sales pipeline. It might not show up on the KPI dashboard directly, but it’s the foundation under everything.

Our 2025 journey was filled with growth, challenges, and aha moments. If you’ve worked in GTM long enough, I guarantee everything above is something that you know in your heart of hearts. However, the work and execution is tough. 

My advice? Whether you’re an individual contributor, operator, executive, founder, CEO, advisor, or even board member, sit down with your team and grade yourselves honestly and thoughtfully on how well you zero in on our ideal customers; execute with precision; build for long-term customer value; extend your reach through partnerships; innovate with AI; and, empower your people.

And above all, focus — on the right market, the right activities, the right relationships, and the right internal investments. 

If we’ve learned anything from 2025, it’s that the sales landscape will always evolve. But if we stay grounded in these lessons, we’ll be ready for whatever curveballs that 2026 throws our way.

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