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 $265000 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.

What We Do

For too long child care programs have been stuck with clunky tools and manual processes falling behind while other industries get all the high-tech toys.Playground is flipping the script. Playground is a proven platform for child care providers to streamline their operations reclaim their time and get back to the joy of teaching and caring. Our all-in-one child care management software manages billing attendance registration and enrollment communication paperwork payroll and more.

Why Work With Us

At Playground we’re a mission-driven high-growth startup where collaboration creativity and entrepreneurial thinking fuel everything we do. We act like owners take initiative and make smart decisions independently every day. Join us to make an impact grow fast and be part of a team that truly values your ideas energy and drive.

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