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SMB SaaS Account Executive

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 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!

About the Role

As an Account Executive at Playground, you will play a critical role in driving new business and expanding our customer base. You will be responsible for the entire sales cycle, focusing on closing deals with qualified leads passed off from our SDR team. This role requires a self-starter with a proven track record in B2B SaaS sales, who is passionate about technology and thrives in a fast-paced environment. Additionally, this position will involve a “player-coach” aspect, where you will be expected to lead by example while mentoring and guiding junior team members.

What You'll Do

  • Closing Deals: Take ownership of qualified leads passed on by the SDR team, guiding them through the final stages of the sales process to successful close.

  • Sales Process Management: Own and manage the entire closing process, from deep discovery to contract negotiation and closing. Develop and execute strategic closing techniques to achieve revenue targets.

  • Customer Engagement: Build and maintain strong relationships with prospects and clients, understanding their business needs and providing tailored solutions.

  • Collaboration: Work closely with marketing, product, and customer success teams to refine messaging, improve the sales process, and deliver an outstanding customer experience.

  • Reporting & Analysis: Maintain accurate records in our CRM system, provide regular updates to management, and contribute to sales forecasting and planning.

  • Continuous Improvement: Stay up-to-date on industry trends, competitive landscape, and product knowledge to effectively position our offerings in the market.

  • Mentorship: Act as a player-coach by actively participating in sales activities while mentoring and supporting junior team members in their development.

What You Need

  • Proven Sales Experience: 3+ years of experience in B2B SaaS sales, with a track record of meeting or exceeding sales quotas. Experience in early childcare is a plus.

  • Tech-Savvy: Strong understanding of SaaS products and the ability to communicate complex technical concepts to non-technical stakeholders.

  • Customer-Centric: A deep understanding of customer needs and the ability to provide consultative sales advice that leads to successful outcomes.

  • Results-Driven: A self-motivated individual who thrives in a high-performance environment and is relentless in pursuing goals.

  • Excellent Communicator: Strong verbal and written communication skills, with the ability to effectively present and negotiate with senior-level decision-makers.

  • Collaborative Team Player: Ability to work cross-functionally and contribute to a positive team culture while maintaining a high level of personal accountability.

  • Adaptable: Comfortable working in a fast-paced, dynamic environment with the ability to quickly pivot when necessary.

  • Player-Coach Mentality: A natural leader who can balance personal sales responsibilities with the mentorship and development of junior team members

Compensation

  • OTE for this position is $150,000 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.

Why Join Playground

  • Competitive salary + equity

  • 3 weeks of PTO

  • Health, vision, and dental benefits

  • $1200/year education stipend

  • Free lunch daily

  • New Macbook

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

  • Help accelerate our mission to make excellent childcare accessible to all!

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 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.

If you want to learn more about what life at Playground HQ is like, check out this post about one of our past recruiting happy hours + our Polaroid wall (our favorite office tradition)!

Average salary estimate

$150000 / YEARLY (est.)
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$150000K

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What You Should Know About SMB SaaS Account Executive, PlayGround

Are you ready to take on an exciting challenge as an SMB SaaS Account Executive at Playground in the vibrant heart of New York City? At Playground, we’re transforming the child care industry with cutting-edge management software, and we’re looking for passionate individuals to join our growing team. As an Account Executive, you’ll dive into the sales cycle, closing deals with qualified leads and expanding our customer base. Your knack for building relationships and understanding client needs will be critical in providing tailored solutions that enable early childhood providers to focus on what they do best. We’re in a phase of rapid growth after securing significant funding and key contracts, making this an ideal time to make your mark with us. You won’t just be selling; you’ll be mentoring and leading junior team members, shaping the future of our sales team. With a competitive compensation package and a supportive, collaborative culture, you’ll thrive in an environment that prizes creativity and initiative. Join us in our mission to make quality child care accessible to all, and help us build a future where technology empowers educators every day. Your journey at Playground awaits—let’s grow together!

Frequently Asked Questions (FAQs) for SMB SaaS Account Executive Role at PlayGround
What are the key responsibilities of an SMB SaaS Account Executive at Playground?

As an SMB SaaS Account Executive at Playground, your primary responsibilities will include managing the entire sales process from lead qualification to closing deals. You'll build strong relationships with clients, understand their needs, and provide customized solutions. Additionally, you will work collaboratively with other teams and mentor junior sales members, ensuring the success of the team while achieving your own sales targets.

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What qualifications are needed to become an SMB SaaS Account Executive at Playground?

To qualify for the SMB SaaS Account Executive position at Playground, candidates should have at least 3 years of experience in B2B SaaS sales with a track record of exceeding sales goals. Strong communication skills and a customer-centric mindset are essential. Familiarity with the early childhood education industry is a plus, as it helps in comprehending the unique challenges faced by our clients.

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How does the sales cycle work for an SMB SaaS Account Executive at Playground?

At Playground, the sales cycle for an SMB SaaS Account Executive involves several stages, beginning with nurturing leads provided by the SDR team. You will conduct deep discovery calls, engage in effective presentations, and negotiate contracts, all while utilizing strategic closing techniques. Maintaining accurate records in the CRM and providing regular updates to management are also integral parts of this role.

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What type of career growth opportunities exist for an SMB SaaS Account Executive at Playground?

An SMB SaaS Account Executive at Playground can expect significant opportunities for career growth, especially as the company expands. You can take on greater responsibilities within the sales organization, mentor newer team members, or explore leadership positions. Additionally, the collaborative culture at Playground encourages personal growth and development, allowing you to excel in your career.

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What is Playground’s Company Culture like for SMB SaaS Account Executives?

Playground fosters a collaborative and inclusive culture that values autonomy, innovation, and personal accountability. As an SMB SaaS Account Executive, you will be part of a supportive team environment where sharing ideas and mentoring one another is encouraged. The vibrant office in Union Square, NYC, enhances the experience, making it a place where you can thrive both professionally and personally.

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Common Interview Questions for SMB SaaS Account Executive
Can you describe your experience in B2B SaaS sales?

When answering this question, outline your relevant work history, focusing on specific achievements that demonstrate your ability to exceed sales targets. Highlight any experience you have in the childcare sector and discuss methodologies or strategies you have successfully employed in past roles.

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What strategies do you use to close deals effectively?

Detail your approach by emphasizing the importance of relationship building, understanding customer needs, and employing strategic negotiation techniques. Use examples from your experiences where these strategies led to successful closes.

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How do you handle objections from potential clients?

Discuss your method for addressing objections: listen actively, empathize, and provide answers tailored to the concerns raised. Share examples where overcoming objections led to closing a significant deal.

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What metrics do you track to measure your sales success?

Talk about key performance indicators (KPIs) such as the number of leads generated, conversion rates, and revenue growth. Stress the importance of using CRM data to inform your strategies and continuously improve.

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How have you mentored junior sales team members in the past?

Share your approach to mentoring, including providing constructive feedback, setting performance goals, and facilitating learning opportunities. Highlight instances where your mentoring had a positive impact on junior members' performance.

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What do you know about Playground’s products and services?

Convey your understanding of Playground’s mission and software offerings, discussing how they address the needs of childcare providers. Mention the competitive landscape and indicate how you believe Playground stands out.

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How do you prioritize your sales activities?

Explain how you assess and prioritize based on the potential value of leads, deadlines, and your overall sales targets. Mention any specific tools or methods you use to manage your time effectively.

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Can you give an example of a challenging sales situation you faced?

Share a specific challenge you encountered, focusing on your thought process and the eventual resolution. Emphasize what you learned from the experience and how it contributed to your growth as a sales professional.

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What is your approach to collaborating with other teams?

Highlight the importance of cross-departmental communication by sharing examples where collaboration led to achieving common goals. Discuss how you maintain open lines of communication with marketing, product, and customer success teams.

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Why do you want to work at Playground as an SMB SaaS Account Executive?

Express your enthusiasm for Playground’s mission to improve childcare and discuss how your values align with the company’s goals. Mention specific aspects of the company culture that appeal to you, and how you believe you can contribute to its success.

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Full-time, on-site
DATE POSTED
April 15, 2025

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