Regional Sales Director

Playground is building the operating system for child care. Our software helps child care providers manage billing, enrollment, parent communication, and more — so they can spend less time on admin work and more time with kids.

We’ve raised millions from top investors, secured statewide partnerships, and work with thousands of schools across the country.

We’re now expanding our sales efforts and looking for an SMB Sales Manager to lead our Mid-Market and SMB teams.

Ready to roll up your sleeves and take on a mission in Early childhood development? As our Regional Sales Director, you’ll be the heartbeat of a tight-knit team of 5-6 Account Executives, driving revenue and crushing quotas in the Mid-Market and SMB space. You’ll jump into the fray with a support quota, tackling overflow or high-stakes deals that need your finesse. Think of yourself as part coach, part strategist, and part closer. No SDR management here; your focus is on leading closers.

• 5-7 years of quota-carrying SaaS sales experience, with at least 2 years leading a team of 5-10 Account Executives.

• Proven ability to build pipelines from scratch in potentially greenfield markets.

• Consistent track record of exceeding sales quotas.

• Low-ego, collaborative, and curious mindset, always seeking ways to improve.

• Startup experience is a plus.

• Manage and coach 5-6 AEs to hit quotas and develop skills.

• Oversee full sales cycle for Mid-Market/SMB accounts, from prospecting to close.

• Handle support quota for complex or high-value deals.

• Collaborate with leadership on sales strategy and market trends.

• Track performance metrics, KPIs, and optimize sales processes.

• Manage Salesforce CRM for accurate pipeline, forecasting, and data integrity.

• Analyze sales data and analytics to inform decisions and improve outcomes.

• Conduct regular 1:1s, training sessions, and performance reviews for team growth.
  

• 5+ years sales management experience in SaaS, with proven team leadership.

• Track record of exceeding sales targets in Mid-Market/SMB segments.

• Expertise in sales methodologies (e.g., Challenger, MEDDIC) and full-cycle selling.

• Proficiency in Salesforce CRM, sales analytics, and reporting tools.

• Bachelor's degree in business, marketing, or related field preferred.

• Strong coaching, negotiation, and deal-closing abilities.

• High emotional intelligence to motivate teams, build rapport, and foster positive environments.

• Ownership mindset with accountability for team results and individual performance.

• Excellent communication, interpersonal, and time management skills.

• Denver-based; able to work in-office 5 days/week.

• OTE for this position is $265,000 subject to standard withholding and applicable taxes

• Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed salary is a guideline, and the salary for this role may be modified.

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• Free lunch daily

• Collaborative and supportive work culture with a high level of autonomy and room for growth

How to Apply: If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground Denver Team is fully in-office in Downtown Denver, CO. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.