VP, Commercial Sales

Role Overview

As VP of Commercial Sales at Serval, you'll own the commercial segment and build the team, systems, and strategy to win it. This is a rare opportunity to join a Sequoia-backed AI company at Series B and define how we go to market across the 1–5k employee segment — a high-volume, high-velocity tier that represents a significant portion of our total addressable market. You'll come in as a third-line leader, building and scaling a layered organization of frontline managers and AEs from the ground up. You'll define segment strategy, territory architecture, and the commercial playbook — then hire the team to execute it. This is not a role for someone who wants to inherit a machine. It's for someone who wants to build one.

You'll partner directly with the founders and GTM leadership to shape commercial strategy, influence product and pricing, and drive predictable, compounding revenue growth.

What You’ll Do

• Organizational Leadership

• Build and scale a third-line commercial sales organization, including frontline managers and AE teams covering the 1–5k employee segment
• Create a performance culture defined by accountability, coaching rigor, and career development

• Segment and Territory Strategy

• Own commercial segment strategy end-to-end: ICP definition, territory design, account segmentation, and coverage modeling
• Define and evolve the commercial go-to-market motion across inbound and outbound channels
• Partner with GTM leadership on pricing, packaging, and deal economics for the commercial tier
• Translate market intelligence into strategic adjustments to territory, headcount, and resource allocation

• Revenue Ownership

• Hold full accountability for commercial ARR, quota attainment, pipeline coverage, and forecast accuracy
• Establish and maintain forecasting discipline and pipeline inspection cadences across the organization
• Drive deal velocity without sacrificing quality — coaching teams to move fast, multi-thread, and close with conviction

• Sales Excellence

• Develop and continuously refine the commercial sales playbook: outbound strategy, discovery frameworks, proof-of-value motions, and champion-led close strategies
• Implement MEDDPICC and other process rigor across the team
• Serve as an executive sponsor in key commercial accounts and model best-in-class selling behavior

• Cross-Functional Partnership

• Collaborate with product, marketing, and engineering to influence roadmap priorities, security and compliance positioning, and commercial-segment messaging
• Partner with Revenue Operations on tooling, reporting, and enablement infrastructure
• Represent the commercial segment at the leadership level — advocating for resources, headcount, and strategic investment

What You’ll Need

• 10+ years of B2B SaaS sales experience, with at least 3–5 years in second or third-line sales leadership

• Proven track record of building and scaling commercial or mid-market sales organizations at high-growth companies (Series B and beyond)

• Deep expertise in segment strategy, territory design, and coverage modeling at scale

• Consistent overachievement across both individual contributor and leadership roles — President's Club, top performer recognition, or accelerated career progression

• Experience selling into IT, Security, and Engineering organizations at the 1–5k employee tier

• Strong command of high-velocity sales cycles (1–3 months) with director to VP-level buyers

• Exceptional executive presence and communication skills — credible with customers, cross-functional partners, and the board

• A builder's mindset: you thrive in ambiguity, create structure where none exists, and raise the bar for everyone around you

Nice to Have

• Experience as an early or founding sales leader who scaled a commercial function from zero

• Management experience at companies known for commercial sales excellence

• Track record of developing managers and building internal career paths within your org

• Deep familiarity with MEDDPICC, Challenger, Command of the Message, and modern sales tech (Salesforce, Outreach, Gong, etc.)

• Comfort leading technical sales motions including proof-of-concepts, security reviews, and API or automation platform discussions

We Offer

• Impact: Be a key player in shaping the success of our product and company

• Growth: Build a fundamentally new AI product offering with the support of our experienced team and investors

• Grow rapidly with the company

• Culture: Join a culture that values innovation, ownership, accountability, and fun

• Compensation Range: $450K - $500K