VP of SMB Sales

What You'll Do

Own Revenue & Pipeline

• Own the SMB bookings number, including new ARR, pipeline generation, and forecast accuracy
• Run a rigorous operating cadence including weekly forecasts, pipeline reviews, and deal inspections
• Drive predictable, repeatable revenue through strong pipeline management and stage discipline
• Oversee SDR performance across inbound and outbound, ensuring strong pipeline coverage and conversion

Build and Lead High-Performing Teams

• Hire, develop, and retain Regional Directors and support them in building high-performing AE teams
• Create a coaching-first culture grounded in call reviews, deal strategy, and continuous development
• Design onboarding programs that ramp AEs quickly in a high-velocity sales environment
• Set and maintain a high talent bar across all levels of the team
• Build clear career pathways from SDR to AE to support long-term talent development

Drive Sales Strategy & Execution

• Reinforce a discovery-first, outcome-driven sales methodology across the team
• Ensure reps run high-quality discovery calls with clear pain identification and outcome mapping
• Elevate demo quality to align with buyer needs and clearly communicate value
• Maintain strong competitive positioning through value-based selling

Lead GTM & Operational Excellence

• Partner with leadership on territory design, quotas, compensation plans, and capacity planning
• Collaborate with Marketing, Product, and Customer Success to improve GTM alignment
• Own Salesforce data integrity, pipeline hygiene, and forecasting accuracy
• Build and refine the SMB sales playbook including talk tracks, objection handling, and ROI frameworks

Support Payments & Revenue Expansion

• Drive adoption of Playground’s integrated payments offering
• Partner with Finance and Payments teams to optimize pricing, margins, and positioning
• Increase payment attach rates as a key revenue lever alongside SaaS

What You Need

• 10+ years of B2B SaaS sales experience, with 6+ years in sales leadership (Director level or above)
• Proven experience scaling SMB sales teams (e.g., growing from ~5 to 20+ AEs)
• Deep experience in high-velocity, transactional sales environments (2–6 week sales cycles)
• Experience with fintech or payments-integrated business models
• Strong Salesforce and data-driven management skills
• Experience designing comp plans, territories, and capacity models

What Makes a Great Fit

• You’ve built scalable sales infrastructure including onboarding, playbooks, and coaching systems
• You think in systems and can diagnose performance issues across people, process, pipeline, and product
• You are passionate about discovery-driven selling and coach it consistently
• You lead through leverage — developing leaders and elevating entire teams
• You bring strong opinions but remain adaptable in a fast-changing environment
• Experience in vertical SaaS or high-growth startup environments is a strong plus

Leadership Traits

• High emotional intelligence and ability to build trust quickly
• Low ego, high accountability mindset
• Strong coaching orientation — you develop people rather than step in for them
• Curious and analytical in how you approach problems
• Bias for action with the ability to move quickly and iterate

Compensation

• On-target earnings for this role are $400,000, including base salary and variable compensation. Final compensation will be determined based on experience, impact, and scope.