GTM Enablement Manager (Senior)

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 providing incredible child 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 work of running a center.

Playground is at an inflection point — and poised to grow extremely fast. We recently raised millions of dollars have 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 projects. If you are excited by the prospect of helping build out Playground’s sales organization and joining a collaborative high-growth startup — please apply!

Playground is hiring our first GTM Enablement Manager (Senior) to design build and run a best-in-class enablement program that accelerates performance across Sales and Customer Success. You’ll sit under our Revenue organization and play an integral role in how we onboard train and continuously upskill our go-to-market teams. This is a perfect role for someone who is looking to join an exceptional team at the earliest stages and have a massive hand in our growth acceleration by streamlining onboarding refining the customer journey and optimizing enablement for our Sales and Customer Success teams.

We’re looking for someone who has owned and run enablement programs end-to-end. You’ll bring expertise in building scalable systems enabling both new hires and tenured reps and driving measurable impact on revenue performance.

This high-visibility high-impact position reports directly to our leadership team and offers the opportunity to build something foundational from the ground up.

Design and Deliver Enablement Programs

• Build and deliver onboarding programs for Sales and Customer Success new hires that combines live facilitation e-learning and real-world application.

• Create scalable playbooks quizzes talk tracks and certification programs that evolve with our product and go-to-market strategy.

• Apply adult learning principles and instructional design best practices to develop engaging effective learning experiences.

• Facilitate workshops and training sessions for team members across multiple experience levels.

Partner Strategically Across Teams

• Collaborate with Sales and CS leaders to identify skill gaps process bottlenecks and enablement opportunities.

• Translate frontline insights into actionable content tools and programs that drive results.

• Ensure teams are equipped with the latest product knowledge customer insights and competitive positioning.

Measure and Optimize Enablement Impact

• Define and track KPIs such as time-to-ramp program adoption and productivity to measure enablement effectiveness.

• Leverage data and feedback to continuously improve content delivery and strategy.

• Partner with internal stakeholders to maintain a centralized enablement hub and single source of truth for GTM teams.

• 5+ years of experience in Sales Enablement Customer Success Enablement or Learning & Development within high-growth B2B SaaS environments

• Experience owning and running enablement programs — not just participating in large pre-built enablement systems.

• Proven track record in building and delivering Sales Academy programs and upskilling initiatives that improve ramp productivity and retention.

• Strong facilitation instructional design and storytelling skills grounded in adult learning principles.

• Demonstrated success designing and delivering programs that improve ramp time productivity and retention

• Excellent communication and presentation abilities across all levels of the organization

• Familiarity with enablement and learning tools (e.g. Salesforce Gong Highspot Seismic or similar platforms)

• A builder mindset: comfortable with ambiguity proactive in creating clarity and passionate about scaling programs from the ground up

• Empathy for both Sales and Customer Success teams with a deep understanding of the customer journey

• Experience supporting channel sales or partner enablement is a plus

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 team is fully in-office in Denver CO. Please make sure you are open to a fully in-person role before applying.

The Playground team is fully in-office in Denver CO so please ensure you’re open to a fully in-person role before applying.

• Competitive salary + equity

• 3 weeks of PTO

• Health vision and dental benefits

• $1200/year education stipend

• 401(k)

• Free lunch daily

• New MacBook and any equipment you need

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

• Help accelerate our mission to make excellent child care accessible to all!

Salary for this position is $110000 - 150000 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 range is a guideline and the range for this role may be modified. Job level and actual compensation will be based on skills experience and interview performance.

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.

Gallery