Account Manager

Location: Chicago, IL - in-office minimum 3 days/week (downtown, starting in 2027)

Compensation: $65K-$80K base + unlimited commissions

Reports to: Commercial Lead

Company: Stridekick

Location: Chicago, IL - in-office minimum 3 days/week (downtown, starting in 2027)

Compensation: $65K-$80K base + unlimited commissions

Reports to: Commercial Lead

Stridekick is a B2B2C preventative health platform that combines gamified health challenges with a curated marketplace of health and wellness products.

Employers and small groups use Stridekick to get their teams moving through fun, competitive challenges. Our marketplace gives users access to thousands of health and wellness products, nearly half of which are HSA/FSA eligible.

We're a small, fast-moving team of fewer than 10, with plans to grow to ~20 over the next two years. Everyone owns their area, works across functions, and moves quickly. If you want to join an early-stage company with real traction, revenue, and a product people love, this is that opportunity.

You’ll own the client relationship from signature through renewal. The core process is already in place, but you’ll be responsible for running it well, improving it, and building on it as we grow.

Onboarding. Launch clients within 8-10 business days of a signed Work Order. Set up their first challenge, train admins, and make sure employees know how to download the app and join.

Managing clients through renewal. Stay close to clients throughout their program, show them what’s working, and keep the relationship moving toward renewal and a longer-term partnership.

Growing participation. Track enrollment and work with clients to increase participation. Identify what’s getting in the way - communication, challenge setup, manager support - and help fix it.

Growing the account. Look for opportunities to expand the relationship, including HSA/FSA marketplace adoption, additional challenges, and more employees or teams participating.

Building engagement across the client. Move the relationship beyond one HR contact by getting more admins, managers, and teams involved.

First 90 days: You know every account in your book, including its size, engagement history, renewal status, and key contacts. You’ve identified under-enrolled accounts and have a plan for each one. You’ve also introduced the HSA/FSA marketplace to clients who weren't aware of it.

By month six: You’ve helped build a consistent way to manage QBRs, renewals, enrollment, and marketplace adoption. The process is clear enough that the next AM can pick it up without starting from scratch.

• You’re hungry and excited to grow accounts and help customers win
• Have 2-5+ years managing B2B accounts, ideally in HR tech, benefits, or SaaS where renewals and expansion are part of the job
• Can look at usage or enrollment data and figure out what’s actually wrong, not just report the number
• Are comfortable pushing a client toward a bigger commitment, not just servicing what they already bought
• Communicate directly. Clients should feel like they’re talking to someone who understands their business, not reading a script
• Are comfortable at a 10-person company where your role will evolve as the company grows

• $65K-$80K base + unlimited commissions
• Health insurance options
• HSA/FSA health spending account
• Unlimited PTO
• Downtown Chicago office