Creating a Sales Strategy Focused on Customer Experience

Something remarkable happened when we started bringing Customer Success leaders into our sales conversations. The traditional sales process transformed into a strategic partnership discussion that benefited everyone involved. After implementing this approach across hundreds of deals, we discovered benefits that went far beyond our initial expectations. Sales teams gained a deeper understanding of post-implementation challenges, which helped them qualify opportunities more effectively. Instead of focusing solely on closing deals, they began asking questions about operational readiness, internal champions, and resource allocation. Prospects received authentic insights into what successful implementation truly requires. Our CS leaders shared real examples of customers who thrived and openly discussed common obstacles they might face. This transparency built trust and helped prospects make informed decisions. Better aligned customer expectations from day one. When CS leaders joined these conversations, they highlighted potential roadblocks and success metrics based on similar customer profiles. This practical guidance helped prospects understand the work required to achieve their desired outcomes. This early involvement proved invaluable for our CS team. They gained visibility into the customer's vision before contracts were signed, allowing them to proactively plan resources and create tailored onboarding strategies. A surprising result was the reduction in "rescue" situations during implementation. We eliminated many issues that typically surfaced months into the relationship by addressing potential challenges during sales discussions. The data supported our approach. Deals that included CS leaders showed 40% higher implementation success rates and 25% faster time-to-value. More importantly, these customers renewed at significantly higher rates. For those considering this approach, start small. Choose strategic opportunities where CS insights could substantially impact the prospect's decision-making process. Document the outcomes and refine your strategy based on that feedback. Great customer relationships begin with the very first conversation.

Something interesting happens when you use design thinking to guide your sales strategy. You actually ditch a sales process for something better: You put your customer’s customer at the heart of every discussion. Your meetings become less about convincing and more about collaborating. You’re figuring out how to redesign a better experience for their customers together. Simple in premise, but hard in practice. That’s because there’s a heavy dose of challenging orthodoxies that’s required on both sides. But business leaders are not always prepared to embrace this way of thinking. A helpful tool to break through the barrier is inverse thinking. Here’s an actual example: Our team met with a top 4 global airline to address improving the customer experience during IRROPS (Irregular Operations — like when flights get delayed due to weather delays). This causes a ton of frustration for customers and a lot of operational headaches for contact centers (the leaders we were engaged with to figure out a better way). Status quo thinking centers around “how do we optimize staffing and lower costs in these events?” Most tech companies would be more than happy to burn through tons of time and effort to explore solutions to that status quo problem. But that’s a HUGE mistake. Challenging the status quo thinking shifts the conversation back to putting the customer at the center of the design strategy, and then brainstorming on ideas to make it a business friendly pursuit, in fact, one that is better and more profitable for the business by doing so. In this particular case, we led with a bold idea: “what if we turned every IRROP into a moment of delight for your customers?” One, it broke through the clutter and established a high-contrast, emotional connection (even if it was a visceral push back). This was an important first step, because it instantly separated us from everyone else they had spoken with (so long competition). But we weren’t done yet… What came next was vital, because we had to have a logical hypothesis and framework to know this bold idea was the right move for their business and not just a big idea we were throwing out there to stand out. Otherwise we would have shattered our credibility and lost the opportunity. We had the data from other major customers to back it up. Not generic case studies, but deep mapping and a maturity model solving this very problem. The next question we asked was the key to unlocking the rest of the engagement, which culminated in a 3-year, $6M deal. Want to know what it was? [due to character limits I share it in the comments ↓] 🐝 

In 2024, we took a radically different approach that drove exceptional net revenue retention (NRR), with all customers renewing and expanding within their first year. Most SaaS companies claim they have a land and expand strategy. But let's be honest—many are just rushing to close initial deals and figuring out expansion later. I’ve seen (and done) this myself as an IC. Here are 3 things we're doing differently to maintain profitability in 2025: (1) Intentional Deal Architecture from Day One We've abandoned the "close now, figure it out later" mentality. Instead, we architect comprehensive deals upfront that map to our customers' growth journey: -Set platform pricing with included user counts -Pre-negotiate expansion user pricing -Define integration pricing tiers -Document future use case pricing This means when a customer starts with Gmail and Salesforce integrations, they already know exactly what adding Microsoft Dynamics or Tableau will cost. No surprises, no painful negotiations – just seamless expansion. (2) Zero Handoffs, Total Accountability. We've eliminated the traditional sales-to-CS handoff that creates gaps in customer experience. The same team that closes your deal stays involved in deployment and ongoing success. This isn't just feel-good stuff – it's practical: -Sales maintains strategic relationships -We deeply understand use cases -We spot expansion opportunities naturally -Early renewal conversations happen organically The result? We're not just vendors – we become strategic advisors helping shape our customers' trial and demo strategies (aka every CRO’s dream state.) (3) Aligned Incentives Drive Better Outcomes Here's something radical: our reps earn the same commission on expansion deals as new business. Why? Because expansion isn't an afterthought – it's core to our strategy. When you remove the artificial divide between new and expansion revenue, teams naturally focus on long-term customer success. 🤙 The Impact Yes, this approach requires more upfront work. You'll spend more time on initial deals. Your sales cycle might lengthen. But the results speak for themselves: >100% customer renewal rate >Every renewal includes expansion >Most customers expand license counts >We're seeing early renewals with expansion The old way of landing deals at all costs then scrambling to expand later is done. Today's market demands intentional, strategic deal architecture that sets both you and your customers up for long-term success. It's time to stop talking about land and expansion and start designing for it from day one.