Account Executive / Sales

Overview

You're selling Recess's marketplace platform to local businesses that offer kids activities—martial arts studios, dance schools, art classes, STEM programs, summer camps. Your job is to convince these business owners that listing on Recess will drive them more enrollments. You're at a 14-person startup, so you'll be building the playbook while executing it.

Role Snapshot

Company Context

Stage: Seed/Early (14 employees, founder-led)

Size: 14 employees

Growth: Actively hiring first sales hire, building out GTM

Market Position: Challenger in a fragmented market (competing with ClassPass Kids, Sawyer, local directories, Google search)

GTM Reality

Pipeline Sources:

• 80% Outbound - You're cold calling and emailing local activity providers. Think studio owners, camp directors, program coordinators.
• 20% Inbound - Maybe some businesses find them through parent word-of-mouth or Google, but don't count on volume.
• 0% Partners - Too early for meaningful partnership channels.

SDR/AE Structure: You're doing everything - research, outreach, demos, closes, onboarding.

SE Support: None. You're showing the platform yourself.

Competitive Landscape

Main Competitors:

• ClassPass Kids (if they're in this space)
• Sawyer
• Heylo/Sawyer competitors
• Google My Business (free)
• Facebook Groups
• Word of mouth

How They Differentiate: Likely parent-focused discovery experience, easier booking, better local market presence.

Common Objections:

• "Parents already find us through Google/referrals"
• "We don't want to pay commission/listing fees"
• "We tried another platform and it didn't work"
• "We're already fully enrolled"

Win Themes:

• Fill empty spots in classes
• Reach parents actively looking (higher intent)
• Less admin work with centralized bookings

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (25%) | Onboarding/CS (20%) | Internal (15%)

Key Activities

• Cold Outreach: You're building lists of local activity providers in your territory. Calling studios during slow hours (10am-2pm, after 7pm). Most don't answer. You're leaving voicemails and sending follow-up emails. Goal is 40-60 touches per day to get 5-10 conversations.
• Discovery Demos: Walking business owners through the platform, usually over Zoom. They're skeptical about another marketplace. You're explaining how parents discover activities, showing the booking flow, addressing "will this actually work for me?" questions. These run 30-45 minutes.
• Closing & Onboarding: Getting them to commit to listing their programs. Then you're often helping them set up their profile, upload photos, input class schedules. This is more hands-on than typical AE work because you need them active on the platform.
• Customer Success Overlap: At 14 people, you're probably checking in with customers to make sure they're getting enrollments, troubleshooting issues, asking for testimonials. The line between sales and CS is blurry.

The Honest Reality

What's Hard

• Small business owners are busy running classes, not answering sales calls. You'll leave 50 voicemails to get 5 callbacks.
• Many are skeptical of marketplaces after trying others that didn't deliver results. You're fighting "we tried this before" fatigue.
• Deal sizes are small, so you need volume. Losing a $2K annual deal doesn't hurt as bad as losing a $100K enterprise deal, but you need to close 10-15/month to matter.
• You're also doing onboarding work that would normally be CS's job. Expect to spend time helping customers get their listings right.
• Early stage means limited brand awareness. Parents might not know Recess exists yet, so your pitch relies on future traffic promises.
• Comp structure is unclear - early AE hires at startups sometimes get lower quotas but also lower OTE until the business scales.

What Success Looks Like

• Onboarding 10-20 new business partners per month (depends on market size)
• 30-40% demo-to-close rate once you figure out the pitch
• Partners stay active and renew because they're getting enrollments
• You help product/marketing understand what resonates with this buyer

Who You're Selling To

Primary Buyers:

• Studio/business owners (deciding on budget and ROI)
• Program directors at larger organizations (summer camps, community centers)

What They Care About:

• "Will this actually bring me customers?" (ROI proof)
• How much does it cost vs. what I'll make back
• Is setup easy or will it take hours of my time
• Can I manage bookings or is this another admin headache
• Do parents in my area actually use this platform

Requirements

• Experience selling to small/local businesses (comfort with high-volume outbound)
• Ability to work independently - no sales manager, no playbook, you're figuring it out
• Comfortable with ambiguity and changing priorities (startup reality)
• Parent or deep understanding of the kids activities space helpful but not required
• Willing to do non-sales work (onboarding help, customer check-ins) until they hire specialists
• Located somewhere you can prospect local businesses effectively (or willing to go remote-first with national outreach)