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.
PlaygroundDenver, CO
