[Hiring] Senior Customer Success Manager @Checkmate

Role Description

We're hiring a Customer Success Manager to own our brand relationships from the first day of onboarding through renewal and expansion. You'll be the person brands trust to make Checkmate work for them: live fast, revenue early, and strong first results that turn into long-term partnerships.

This is a high-ownership role on a small team. You'll carry your own book of brands, run those relationships end to end, and sit close to the revenue we deliver. If you like owning outcomes, moving fast, and being the reason a brand stays and grows, you'll thrive here.

What You’ll Do

• Onboarding & Activation
  • Lead onboarding for new brands, from kickoff through go-live
  • Configure each brand's offers, channels, and audiences for their goals
  • Set success metrics and a clear first-30-days plan with every brand
  • Get brands to first revenue quickly and cleanly
• Account Management
  • Own a book of brands as their main point of contact
  • Run regular check-ins, business reviews, and performance recaps
  • Track account health, usage, and renewal timelines
  • Get ahead of risk before it reaches a renewal
• Retention & Growth
  • Own renewals across your book
  • Identify expansion opportunities and build the case with data
  • Turn strong results into case studies and references
• Cross-Functional Execution
  • Work with Rev Ops to translate performance into account actions
  • Bring brand feedback to Product and Ops, and flag what matters
  • Partner with Sales on clean handoffs and account planning
• Build for Scale
  • Help standardize onboarding playbooks and account templates
  • Improve CS workflows and reduce manual steps
  • Contribute to repeatable processes as the team grows

Who You Are

• You build trust fast, and people want to keep working with you
• You're energized by ownership and comfortable being the single point of accountability for an account
• You read the data, find the story in it, and turn it into a recommendation a brand will act on
• You stay organized and move fast when you're juggling a lot at once
• You're genuinely curious about ecommerce and what makes brands grow

What You Bring

• 3+ years in customer success, account management, or partnerships, ideally in martech, ecommerce, or SaaS
• A track record of retaining and growing a book of business
• Comfort with performance data and the ability to turn metrics into a clear narrative
• Sharp communication, whether you're running a business review or writing a follow-up
• Bonus: you already know the DTC stack (Klaviyo, Attentive, Shopify) or have worked with DTC brands

Why Join Checkmate

• Solve real problems: Help DTC brands unlock millions in missed revenue
• Work with top brands: Partner with category leaders like Brooklinen, Quay, and ColourPop
• Growth opportunity: Exposure to AI, martech innovation, and fast-moving eCommerce

Compensation & Benefits

• Competitive base salary + commission package
• Equity in a fast-growing, venture-backed company
• Traditional medical/dental/vision/other healthcare coverage
• 4 weeks PTO + health days
• 401k plan
• Monthly gym membership reimbursement
• Company retreats and team get togethers
• Remote-first culture (preference for those near major cities - NYC, LA, SLC, Miami, Chicago, etc.)