Repositioning a Mature SMB Tool into an Enterprise Platform
How I led a strategic market pivot at Yesware—shifting from a Gmail-centric sales tool to a Microsoft Outlook–anchored enterprise platform—and grew ARR from $6M to $10M while positioning the company for acquisition.
Strong Brand, Structural Ceiling
When I joined Yesware as VP of Product & Design, the company had real brand recognition and a loyal user base—but growth had stalled. ARR sat at approximately $6M, driven almost entirely by SMB credit-card revenue with high churn and limited expansion potential.
The product was deeply anchored in Gmail. But enterprise sales teams overwhelmingly standardize on Microsoft Outlook, operate on annual purchasing cycles, and require security compliance before a deal can even begin. The company's ecosystem alignment was fundamentally mismatched with enterprise reality.
The business needed to move upstream—toward larger, more durable contracts—without losing its core while building the credibility and platform capabilities enterprise buyers demanded.
My Role: VP of Product & Design
Reporting directly to the CEO and serving as a core member of the executive team, I owned enterprise-wide product and design strategy across six cross-functional teams—four feature teams and two horizontal teams covering Security and DevOps. I participated in weekly executive meetings, board presentations, and operated as a trusted strategic partner across Product, Sales, Marketing, and Customer Success.
SMB Revenue Ceiling
Heavy reliance on monthly credit-card subscriptions created structural churn exposure. SMB customers churned at rates that made it nearly impossible to build durable ARR growth or expand into larger accounts.
Ecosystem Misalignment
The product was built for Gmail, but enterprise sales organizations run on Microsoft Outlook. Without native Outlook support, Yesware couldn't even get into the consideration set for the enterprise deals it needed.
No Security Credibility
Enterprise IT buyers require SOC 2 compliance as a baseline. Without it, no amount of product quality could advance a deal past procurement. Security was the hard wall blocking enterprise revenue.
Execution Fatigue
The organization relied on heavy annual and quarterly planning cycles that created upfront planning debt, reduced agility, and drained engineering momentum. The team had slowed down inside a mature operating structure.
Reframing the Question to Find the Real Opportunity
The most important strategic move wasn't a product decision—it was a reframe. I led the team through a deliberate shift in perspective: we stopped asking "how do we optimize the SMB funnel?" and started asking "how do we become an enterprise-grade revenue platform aligned to Microsoft's ecosystem and annual enterprise buying cycles?"
That shift changed everything downstream—roadmap priorities, platform decisions, partner relationships, and GTM motions all flowed from that new question. Discovery work with enterprise prospects validated the hypothesis quickly: Outlook presence and SOC 2 compliance weren't differentiators, they were table stakes.
I partnered closely with Sales and Customer Success to map where deals were stalling, which customers had expansion potential, and what it would take to close a flagship enterprise account. The pattern was consistent and the path was clear.
Enterprise Prospect Interviews
Direct engagement with target enterprise buyers to understand deal blockers and requirements.
Pipeline & Churn Analysis
Data-driven review of where ARR was stalling, expanding, or churning to inform prioritization.
Ecosystem Research
Market analysis confirming enterprise sales team standardization on Microsoft Outlook and annual procurement motions.
Security Gap Assessment
Mapped the compliance requirements blocking enterprise deals and scoped the SOC 2 execution plan.
"Enterprise buyers don't evaluate features first—they evaluate trust. SOC 2 wasn't compliance theater. It was the key that unlocked the room."
A Strategic Thesis That Changed Everything Downstream
Once the strategic thesis was clear—become an enterprise-grade revenue platform aligned to the Microsoft ecosystem—every downstream decision had a filter. We could evaluate roadmap investments, partnership decisions, and GTM priorities against a single coherent direction rather than fragmented SMB optimization.
Ecosystem-First Roadmap
I anchored the product roadmap around the Microsoft ecosystem—prioritizing Outlook-native functionality, enterprise-ready integrations, and annual procurement alignment. This wasn't just feature development; it was a deliberate repositioning of where Yesware sat in the market.
Investments that deepened Gmail dependency were deprioritized. Investments that built Outlook depth, enterprise workflow integration, and administrative controls were fast-tracked. The roadmap became a strategic document, not a feature list.
SOC 2 as a Revenue Lever
I made the case to the CEO and executive team that SOC 2 wasn't a compliance cost—it was a revenue unlock. We dedicated a full engineering team to a focused six-month execution plan and partnered directly with a flagship enterprise prospect throughout the process.
Dedicated Engineering Team
Full team allocation to compliance work rather than splitting attention across the org
Prospect Partnership
Aligned compliance scope directly with Bank of Montreal's enterprise requirements
Reusable Foundation
Built security credibility that scaled across the entire enterprise pipeline, not just one deal
Rebuilding Execution Energy in a Mature Organization
Strategic clarity is necessary but not sufficient. A mature organization with execution fatigue needs a new operating rhythm to translate strategy into delivery. I replaced monolithic annual and quarterly planning with Shape Up–inspired six-week cycles and structured cooldown periods.
Securing buy-in from senior engineering leadership was the critical unlock. I invested time in sustained engagement—not a single meeting, but an ongoing dialogue—until the model was genuinely understood and endorsed. Once engineering leadership was aligned, adoption was fast.
The culture shift was equally important. I operated as a player-coach: managing enterprise escalations directly, leading churn-risk account interventions, coaching PMs and designers, and making difficult people decisions where needed. The team moved from reactive to deliberate.
The New Operating Model
The result: faster decision velocity, sharper prioritization, improved engineering morale, and higher roadmap clarity for GTM partners. Execution regained its rhythm.
A Strategic Pivot That Transformed the Business
Moving a mature SaaS business upstream requires making intentional tradeoffs—reducing investment in the existing SMB base to fund the platform and compliance work enterprise buyers require. These aren't easy calls, but the business needed a new trajectory.
Over approximately two years, the repositioning drove measurable results: ARR grew from ~$6M to ~$10M, the company landed its first significant enterprise contract, and the business was positioned for successful acquisition.
Revenue Transformation
Shifted the ARR mix from volatile SMB credit-card revenue toward durable enterprise contracts. The Bank of Montreal deal alone represented a contract structure—annual, committed, expanding—that dozens of SMB accounts couldn't match. Enterprise repositioning created compounding value density.
Organizational Health
Restored execution energy in a mature, declining organization through operating model transformation and culture work. The team went from reactive to deliberate—faster decisions, clearer priorities, and higher morale across Product, Engineering, and Design.
Facing a Similar Challenge?
Let's discuss how I can help transform your product strategy and drive measurable business outcomes.
Get in Touch