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Sales Manager

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 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 for rapid growth. We recently raised millions of dollars, secured several statewide contracts, and are working with thousands of schools across the country. Our founders were recently honored as Forbes 30 Under 30.

We are a team of owners, unafraid to dive into large, complex projects. If you’re excited about helping build Playground’s sales organization and joining a collaborative, high-growth startup, we want to hear from you!

What You’ll Do

  • Manage and coach a team of Account Executives & Sales Development Representatives 

  • Improve rep performance through call reviews, live coaching, and structured feedback

  • Optimize the sales funnel, improving demo-to-close conversion and time to close

  • Partner with RevOps to forecast accurately, track KPIs, and drive pipeline visibility

  • Collaborate with Marketing to ensure tight lead handoffs and iterate on what makes a high-quality lead

  • Collaborate with Customer Success to ensure customers are properly sold and handed off well

  • Refine sales processes across discovery, qualification, objection handling, and competitive differentiation

  • Support hiring, onboarding, and scaling of the sales team as we grow—including joining sales calls to model best practices and stay close to the pitch

What Makes a Great Fit

  • 2–5 years of experience managing high-performing sales teams in a B2B SaaS environment

  • Must have sold software to SMBs in a vertical SaaS (vSaaS) context

  • Deep understanding of SMB buyer psychology and how to run a consultative sale with time-constrained, cost-conscious decision-makers

  • Track record of success with inbound sales motions, and comfort coaching early outbound reps

  • Proficient in Salesforce for pipeline management and optimization

  • Excited to roll up sleeves to help build and scale systems, playbooks, and processes

  • Excellent communicator, motivator, and coach who leads by example

  • Metrics-driven and confident owning weekly forecasting and team performance

Why Join Playground

  • Competitive salary + equity

  • 3 weeks of PTO

  • Health, vision, and dental benefits

  • $1200/year education stipend

  • 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!

Compensation

The annual OTE (60/40 split) for this position is $135,000 - $155,000, subject to standard withholding and applicable taxes. Job level and actual compensation will depend on individual qualifications assessed during the interview process (skills, prior experience, potential impact, scope of role, and work location). The listed range is a guideline and may be modified.

What Makes a Great Fit

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 Union Square, NYC. 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.

Average salary estimate

$145000 / YEARLY (est.)
min
max
$135000K
$155000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Sales Manager, PlayGround

Are you ready to take your sales career to the next level? Join Playground as a Sales Manager! We are on a mission to make excellent child care accessible to everyone, and we're looking for someone like you to help build our sales organization. In this role, based in the heart of New York City, you’ll manage and coach a rockstar team of Account Executives and Sales Development Representatives, driving performance through impactful coaching and feedback. You'll have the opportunity to optimize our sales funnel and work closely with our RevOps and Marketing teams to ensure high-quality leads are being handled efficiently. If you thrive in a collaborative, high-growth startup environment, you’ll find Playground an exhilarating place to grow your career. With 2-5 years of experience managing sales teams in a B2B SaaS context, you’ll understand the nuances of selling to SMBs and demonstrate a strong track record in inbound sales motions. You’ll truly become an integral part of our mission as we elevate child care through our best-in-class management software. You'll enjoy competitive compensation, benefits, a generous PTO policy, and the chance to help us scale while enjoying free daily lunches in our supportive company culture. If this sounds like your next big adventure, we’d love to hear from you!

Frequently Asked Questions (FAQs) for Sales Manager Role at PlayGround
What are the main responsibilities of the Sales Manager at Playground?

As a Sales Manager at Playground, you will manage and coach a dedicated team of Account Executives and Sales Development Representatives. Your main responsibilities will include enhancing rep performance through coaching, optimizing the sales funnel for improved conversion rates, partnering with RevOps for accurate forecasting, and collaborating closely with Marketing and Customer Success. Additionally, you'll refine sales processes and support the onboarding and hiring of new sales team members.

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What qualifications are required for the Sales Manager position at Playground?

To excel in the Sales Manager role at Playground, you need 2-5 years of experience managing high-performing sales teams specifically in a B2B SaaS environment. A track record of selling software to SMBs in a vertical SaaS context is essential. Moreover, you should possess a deep understanding of SMB buyer psychology and experience in consultative sales, alongside strong coaching skills and proficiency in Salesforce.

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What can I expect from the company culture as a Sales Manager at Playground?

At Playground, you'll be embraced by a collaborative and supportive work culture that values ownership, craftsmanship, and empathy. As a Sales Manager, you’ll enjoy a high degree of autonomy, the ability to make impactful decisions, and ample opportunities for personal and professional growth. Our environment is designed to fuel innovation and encourage proactive contributions from all team members.

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What benefits and compensation does the Sales Manager position at Playground offer?

The Sales Manager position at Playground offers competitive compensation packages with an OTE of $135,000 - $155,000. Along with a salary, employees receive equity, 3 weeks of PTO, comprehensive health, vision, and dental benefits, a $1200 yearly education stipend, and even free daily lunches. You'll also be equipped with the latest tools, including a new MacBook, to ensure your success in the role.

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How does Playground support the growth and development of its Sales Managers?

Playground is committed to fostering growth and development for all team members. As a Sales Manager, you’ll play a key role in hiring and onboarding new sales talent while also modeling best practices during calls. The company encourages continuous learning through its education stipend, providing access to workshops and courses that align with your professional development goals. You’ll also benefit from structured feedback opportunities to enhance your coaching and leadership skills.

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Common Interview Questions for Sales Manager
How would you describe your management style as a Sales Manager?

In interviews, it's crucial to articulate a management style that focuses on collaboration and empowerment. You might say, 'I believe in leading by example and fostering an environment where team members feel supported and motivated. I prioritize open communication and regular feedback to help my team achieve their goals while also setting clear expectations and accountability.'

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Can you give an example of how you've improved sales performance in your previous roles?

When answering this question, provide a specific example. You might say, 'In my last position, I identified that our demo-to-close conversion rate was lower than expected. I implemented regular call reviews and live coaching sessions. This led to a 20% increase in conversion rates within three months, showcasing the impact of continuous coaching and structured feedback on sales performance.'

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What strategies do you use to optimize the sales funnel?

You could respond by outlining a multi-faceted approach, such as: 'I focus on identifying lead quality, streamlining our qualification process, and ensuring that our sales team is equipped with effective objection-handling tactics. Additionally, I believe in leveraging data analytics to monitor our funnel's performance and making adjustments as needed for maximum efficiency.'

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How do you collaborate with other departments to enhance sales processes?

Describing collaboration is key. You could say, 'I actively collaborate with our RevOps team to ensure data accuracy for forecasting, while also working closely with Marketing on lead generation strategies. Regular inter-departmental meetings allow for alignment on goals and processes, and I seek feedback from Customer Success to refine our sales techniques based on customer experiences.'

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How do you handle underperforming sales team members?

It's essential to approach this with empathy. You might answer, 'I first engage in one-on-one discussions to understand their challenges. I then provide tailored support, whether through additional training, coaching sessions, or adjusting targets to realistic expectations. My goal is to uplift each team member while also holding them accountable for their performance.'

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What metrics do you prioritize when assessing sales team performance?

You could respond, 'I focus on metrics such as conversion rates, average deal size, sales cycle length, and overall quota attainment. Additionally, I analyze the effectiveness of the sales funnel stages to identify where improvements can be made, ensuring that we have a comprehensive view of our team's success and areas for growth.'

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What role does technology play in your sales management approach?

You might say, 'Technology is integral to my sales management. I utilize CRM systems like Salesforce for tracking performance and data analytics. These tools allow me to visualize sales processes, manage pipelines effectively, and enable my team to focus on selling rather than administrative tasks.'

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How do you ensure continuous learning and development for your sales team?

You could say, 'I prioritize a culture of continuous improvement by establishing regular training sessions that cover sales techniques, product knowledge, and market trends. I also encourage team members to participate in industry seminars and leverage our education stipend for further learning opportunities.'

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Describe a time when you had to change your sales strategy. What led to that decision?

When answering this, share a relevant experience. For example, 'When our target market shifted, I had to pivot our sales strategy to focus on a new customer segment. We conducted market research that highlighted the need for a tailored approach, leading to a successful transition that ultimately increased our pipeline significantly.'

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What motivates you as a Sales Manager?

You might express your motivations by saying, 'I am driven by the impact that a high-performing sales team can have on a company's growth and success. I find great satisfaction in developing talent and seeing my team achieve and exceed their goals, which ultimately results in the company's mission being realized.'

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DATE POSTED
April 12, 2025

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