Sales Ops + GTM Lead

What is Checkmate?

Checkmate is a consumer app and data company that helps brands connect with shoppers more effectively. We use real-time shopping behavior, our “data network”, to target, retarget, and convert high-intent customers.

Here’s a quick snapshot of what we’ve accomplished over the past few years.

• We have millions of users that use our app to find personalized deals. We’ve been the #1 app within the App store 2x times.
• Hundreds of brands use Checkmate to reach their customers more effectively, drive retention, and build personalized marketing flows — all through our network, which includes our app, SMS, email, and browser extension.

Our north star is simple: help brands retain users longer and deliver more personalized deals - while ensuring consumers get the best value from every purchase.

Rev Ops at Checkmate

Operations at Checkmate is still a relatively new function. We’re moving beyond the first phase - focused on retention and delivering the essentials - and stepping into a period of growth. Now it’s time to scale, and you’ll be leading the charge in shaping how Sales, Onboarding, and Customer Success evolves. Your sole job: keep the pipeline flowing from beginning to end.

Who we’re looking for?

Sales Ops expert - up with the times, knowledgeable about sales automation, Clay, webhooks, multi-touch campaigns - very detail oriented and disciplined - can predictably track deals through a lifecycle and forecast expertly. Obsessed with the pipeline, not just from a sales lens, but retention as well.

“Put your head over the onion.” Don’t worry - all it means is, be willing to dive in and do the work. The ideal person isn’t afraid to start talking to clients in Week 1, dig into the data by Week 2, and begin strategizing on how to deliver real value by Week 3.

Roles & Responsibilities

• Disciplined + perfectionist: You have high attention to detail, care about processes being followed (while simultaneously making them easy to navigate), and you’re a QA-zar and need everything perfect (data-hygiene is 911) 
• You automate everything - provide multi-channel visibility on deals (Slack, Hubspot, Email), and believe a small and informed sales team is better than a 300-person org.
• Be able to forecast reasonably QoQ. Can pivot as assumptions change. No static models
• Can write up a playbook for a product, target ICPs, and win TAM and even help expand product offerings beyond TAM
• You’re a master of making complex things sound super easy, both verbally and through text.
• You have a confident presence - comfortable talking shop with CEOs, CMOs, and Heads of departments.
• Data driven - while you don’t have to be able to query data yourself, you should be able to interpret data, understand the story it tells, and present insights clearly and cohesively

• Skills needed: Ability to deliver financial forecasts, some finance background is nice to have.
• Proficiency in CRMs (Hubspot), Clay, sales automations (email, SMS), Linkedin Ads preferred.
• Loves start-ups and thinks like an owner / founder
• 4-7 years in biz ops or strategy
• Comfortable with data: Excel/Google Sheets, used BI tools like Amplitude, Looker, or Tableau in the past
• Note: If you think you can “rock” this roll, just apply. I promise we’ll read every resume and consider everyone

Hiring process

• Assessment. <2 hrs
• Meet with Shounak, Head of Ops (who you’ll report to)
• Round-table interview - Sales team
• Meet with co-founders, Harry and Rory
• Meet with Shounak again

• Salary range ($100,000 - $145,0000) // Just apply <: ) 
• Healthcare + dental + vision
• 401k
• Company retreats
• 4 weeks PTOs and health days
• Gym membership comped
• US remote - Los Angeles or New York City preferred