Upsell Representative (Payroll Product Flagship) at Arketa

Arketa is building the operating system for modern fitness and wellness. Their mission is to make wellness more accessible by empowering studios and wellness entrepreneurs to grow beyond in-person classes. They provide a powerful, all-in-one platform to manage and scale hybrid wellness businesses, whether online, in-person, or both.

With Arketa, studios can manage schedules, accept bookings and payments, build on-demand video libraries, host retreats, run automated marketing, and launch fully branded apps and websites. They make it simple for founders to deliver a seamless, professional experience across every customer touchpoint.

About the Role

As our Upsell Representative, you'll grow revenue inside the existing customer base by selling Arketa's full suite of add-on products, including their branded app, website, marketing, and phone products. As the flagship of this role, you'll pioneer the brand-new Payroll product as one of the very first people to sell it.

You'll help shape the pitch, the playbook, and the motion from the ground up. Working closely with Customer Success, you'll identify the right accounts, run tailored value conversations, and own the full expansion cycle from opportunity to close. This is a high-impact, ground-floor role for a seller who is energized by brand-new products and a clear path to grow revenue per customer.

About the Team

You'll sit on the Sales team and work shoulder to shoulder with Customer Success, who know the install base better than anyone and will be your closest partner in spotting the right accounts. You'll also work directly with the Payroll and Product teams, feeding real customer signal back into a product that is still taking shape.

This is a small, fast-moving team where the person doing the work also writes the playbook. If you like having a real say in how a motion gets built rather than inheriting one, this is that seat. You'll be given all inbound expansion interest, so your time goes into conversations and closing, not cold prospecting.

What You'll Do:

• Own the full expansion cycle, from spotting the opportunity to close, for Arketa's add-on products across the existing customer base.

• Pioneer the brand-new Payroll product as the flagship, alongside the full add-on suite (branded app, website, marketing, phone, and more).

• Partner with Customer Success to identify and prioritize the right accounts using product usage and account data.

• Run tailored demos and ROI conversations that connect each add-on to the studio's goals.

• Meet and exceed your expansion and upsell quota.

• Maintain accurate pipeline management and expert-level forecasting in HubSpot.

• Help build the playbook: messaging, objection handling, and best practices for brand-new products.

• Feed structured product feedback back to the Payroll and Product teams.

• Use AI (Claude) to research accounts, personalize outreach, and move deals faster.

• Be an exemplary ambassador for Arketa, both internally and externally.

What Success Looks Like:

• 30 days: Onboarded and fluent in Payroll, the add-on suite, and the install base. You're shadowing Customer Success and learning the accounts.

• 60 days: An active expansion pipeline is built, your first Payroll and add-on deals are closed, and the early playbook is taking shape.

• 90 days: Consistently at or above expansion quota with reliable forecasting, and you have a repeatable motion for selling add-ons into the base.

What We're Looking For:

• 2+ years in SaaS sales, account management, or expansion and upsell, ideally selling into an existing customer base.

• Comfortable being an early seller of new products, where you help define the pitch and playbook.

• Strong at value and ROI conversations, and at multi-product storytelling.

• Excellent pipeline discipline and forecasting. You keep HubSpot immaculate.

• A relationship-led seller with a track record of exceeding quota.

• Strong written and verbal communicator. Scrappy and resourceful.

• Hands-on with AI (Claude) and comfortable with a modern sales stack (HubSpot, Avoma, Nooks).

• Passion for fitness, wellness, and helping studios grow.

• BA/BS preferred.

Bonus:

• Exposure to payroll, fintech, accounting, or embedded finance products.

• Experience selling payroll or financial software to small businesses.

• Experience launching a brand-new product line or expansion motion.

• Familiarity with the wellness and studio space (Mindbody, WellnessLiving, Mariana Tek, Momence).

• Based in or near NYC, where the office is.

You Should Apply If:

• You want to be the first person to ever sell a product and want your fingerprints on the pitch and the playbook.

• You'd rather work a warm install base and inbound interest than grind cold outbound.

• You're motivated by uncapped commission and want a clear line between your effort and your earnings.

• You're comfortable with ambiguity and can build structure where none exists yet.

• You're mission-driven and excited about wellness becoming more accessible.

You May Not Want to Apply If:

• You need a finished playbook, established messaging, and proven objection handling on day one.

• You prefer net-new logo hunting over expanding existing relationships.

• You want a large sales org with clear specialization and a defined promotion ladder already in place.

• You want a slower pace or a more established later-stage environment.

What We Offer:

• Ownership and Opportunity for Advancement

• Competitive Salary and Stock Options and uncapped, performance-based commission

• Unlimited PTO

• Medical, dental, and vision health insurance

• Fitness Class Reimbursement

• Parental Leave Policy