---
title: 'VP of SMB Sales at Playground'
canonical: 'https://feeny.ai/job/vp-of-smb-sales-playground-denver-ma7v9atzgr0d'
type: 'job'
last_seen: '2026-09-06'
---

# VP of SMB Sales at Playground

- **Company:** Playground
- **Location:** Denver, CO
- **Compensation:** $400k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-04-23
- **Last confirmed live:** 2026-09-06
- **Apply:** https://jobs.ashbyhq.com/playground/a314ccc5-ac2b-45d2-9826-12e57c4000bb/application

**Skills:** B2B SaaS Sales, Salesforce, Pipeline Management, Forecasting, Territory Planning, Compensation Plan Design, SMB Sales, High-Velocity Sales, Transactional Sales, Fintech Sales, Payments-Integrated Business Models, Vertical SaaS Sales

> The VP of SMB Sales owns revenue delivery and go-to-market strategy for the SMB segment, including single-location centers and small multi-site operators. This executive role involves scaling the sales organization, leading Regional Directors and SDRs, and driving pipeline generation and forecast accuracy in a high-...

## Job description

## ABOUT PLAYGROUND

Playground is working to make excellent child care accessible to all. Playground has built best-in-class software to manage all aspects of running a child care business. We believe that providers should focus on delivering incredible care — the kind of work that only people can do — and that software should manage the rest. We’re building the child care management platform that eliminates the administrative burden of operating a center.

Playground is at an inflection point — and poised to grow extremely fast. We’ve recently raised millions in funding, secured several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 Under 30.

We are a team of owners who are not afraid to dive into large, complex challenges. If you’re excited by the opportunity to scale a high-performing sales organization at a mission-driven, high-growth startup — we’d love to meet you.

## ABOUT THE ROLE

Playground is hiring a VP of SMB Sales to own revenue delivery and go-to-market strategy for our SMB segment — including single-location centers, small multi-site operators, and family childcare providers across the country.

This is our largest and fastest-growing segment, and the foundation is working. Your role is to scale it — without breaking what makes it successful.

You’ll operate across three core areas: leading the business, developing your people, and building the systems that allow us to scale. You’ll oversee Regional Directors and SDR leadership, ensuring strong pipeline generation, disciplined execution, and consistent performance across the funnel.

This is a pure leadership role — your success is measured by your team’s success. You’ll report directly to the Head of Sales and act as a key partner on org design, territory planning, pricing strategy, and overall GTM execution.

## 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

## WHY JOIN PLAYGROUND

- Competitive salary + meaningful equity
- 3 weeks PTO
- Health, vision, and dental benefits
- $1,200/year education stipend
- Free lunch daily
- A strong sales culture with defined methodology and a robust playbook
- High-growth environment with significant opportunity for impact and advancement

## 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.

## About Playground

## Company Overview
- **One-liner**: Playground provides an all-in-one child care management platform that streamlines operations—including billing, attendance, registration, communication, payroll, and AI-powered assistance—for early education providers.
- **Entity Type**: Private (early-stage startup; funding details not fully disclosed)
- **Headquarters**: New York City, New York, USA (with a second office in Denver, Colorado)
- **Founded**: 2021
- **Founders**: Daniel Andrews, Josh Andrews, and Sasha Reiss

## Core Business
- **Primary industry**: Child care management software / Early education technology
- **Target customers**: B2B – child care programs of all sizes (home-based, centers, multi-site, and government)
- **Mission/purpose**: To make excellent child care accessible to all by giving providers the tools to focus on teaching and caring, not administration.

## Products & Services
- **Playground Platform (Core)**: SaaS platform handling attendance tracking, billing, registration, communication, paperwork, payroll, and expense management. Includes predictive enrollment forecasting and free data migration.
- **Camber (AI Employee)**: An AI agent that answers phone calls, qualifies leads, handles admin tasks, drafts messages, processes refunds, reconciles subsidies, and answers staff/family questions using the program’s handbook and state licensing rules.
- **Payroll (Built-in)**: Full-service payroll with tax filing and time tracking tailored for child care.
- **Learning Module**: Tools for activity planning, milestone tracking, and family sharing.

## Market Standing
- **Valuation**: Not publicly available
- **Key Metric**: Estimated annual revenue between $5 M and $25 M (LinkedIn estimate). Serves 5,000+ child care programs and 500,000+ families across all 50 U.S. states.
- **Notable Investors/Partners**: Not disclosed publicly (careers page mentions “amazing investors” but no names listed)
- **Growth Signals**: LinkedIn follower base grew 98.9% year over year; strong brand presence with 300,000+ users on the platform; continuously expanding AI capabilities (Camber launch); hiring across engineering, sales, customer success, and marketing for both NYC and Denver offices.

## Competitive Advantages
- **AI-first solution** – Camber acts as a virtual part-time hire, handling inquiries and admin tasks that previously required separate tools or staff.
- **All-in-one integration** – Replaces multiple legacy tools (separate billing, attendance, payroll, communication) with a single platform designed specifically for child care.
- **Predictive analytics** – Forecasting tools help centers anticipate enrollment openings and optimize capacity.
- **Free data migration** – Low switching friction for new customers.
- **Deeply rooted in the industry** – Founders grew up in a child care family and built the product to solve real pain points they experienced firsthand.

## Strategic Focus
- **AI expansion** – Deepening the Camber assistant’s capabilities (inquiry handling, staff support, reporting) and integrating it more tightly with core operations.
- **Scaling across segments** – Serving programs of all sizes, from home-based daycares to large multi-site and government-run centers.
- **Product unification** – Continuing to consolidate previously fragmented workflows (payroll, billing, learning) into a single, intuitive platform.
- **Geographic coverage** – Already active in all 50 states; likely targeting deeper penetration and perhaps eventual international expansion.

## Why Work Here
- **Transparent culture** – Leadership holds twice-monthly founder-led all‑hands, sends weekly CEO updates, and runs open “Ask Me Anything” office hours. Biannual anonymous employee surveys are shared with action plans.
- **Ownership and autonomy** – The company values “high agency people” who act like owners; employees are encouraged to act independently and intelligently.
- **Hybrid/in‑office model** – Teams work from offices in New York City (downtown) and Denver (downtown). On‑site days are the norm, and the interview process includes a paid half‑day onsite.
- **Perks & benefits**:
  - Equity for all full-time employees
  - Comprehensive health, dental, and vision plans
  - Free daily lunch ($4,800/year value)
  - $1,200 annual education stipend
  - Generous paid time off
  - MacBook + desk setup stipend
  - Discounts on child care supplies (diapers, wipes, etc.)
- **Meaningful mission** – Employees build tools that directly free up child care providers’ time, enabling them to focus on children and families.

## Sources
1. [tryplayground.com – Homepage](https://www.tryplayground.com/)  
2. [Playground Careers page](https://www.tryplayground.com/careers)  
3. [Playground About page](https://www.tryplayground.com/about)  
4. [LinkedIn Company Profile](https://www.linkedin.com/company/tryplayground)  
5. [Built In Colorado – Workplace Perception](https://www.builtincolorado.com/company/playground-tryplaygroundcom/faq/workplace-perception)

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