VP of SMB Sales

Playground•Denver, CO

About The Position

Playground is seeking a VP of SMB Sales to lead revenue delivery and go-to-market strategy for its SMB segment, which includes single-location centers, small multi-site operators, and family childcare providers nationwide. This is Playground's largest and fastest-growing segment, and the role focuses on scaling it effectively. The position involves leading the business, developing the team, and building scalable systems. The VP will oversee Regional Directors and SDR leadership, ensuring strong pipeline generation, disciplined execution, and consistent performance. This is a leadership role reporting directly to the Head of Sales, with key partnerships in organizational design, territory planning, pricing strategy, and overall go-to-market execution. Playground is a high-growth startup focused on making excellent child care accessible through best-in-class software, having recently secured significant funding and statewide contracts.

Requirements

10+ years of B2B SaaS sales experience
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

Nice To Haves

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
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

Responsibilities

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.
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.
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.
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.
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.