Senior Customer Success Manager (CSM)

About Checkmate

Checkmate is a multichannel offers network loved by 100M shoppers and 450+ leading brands.

For shoppers, it's how they discover and save on the brands they love, with personalized cashback and offers across our app, email, and SMS.

For brands, it's a new channel to reach and convert high-intent shoppers they can't find anywhere else. Hundreds of leading brands, including Brooklinen, Quay, and Summer Fridays, use Checkmate to drive incremental revenue, paying only when we deliver a sale.

The combination is rare: a consumer product shoppers love and a performance engine brands depend on, powered by AI that knows exactly who to reach and how to convert.

Backed by GV, Mantis VC, and DST Global. We're a remote-first team with hubs in LA and NYC, and a preference for hiring in or near major cities.

The Role

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

Why This Role Matters

Brands come to Checkmate for incremental revenue. You're the person who makes sure they get it, and that they stay to get more. When your brands are live, growing, and renewing, the whole business compounds. This is one of the most direct lines to revenue we have, and it's yours to own.

Requirements

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

Benefits

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.)