Scaled Customer Success Manager

Workyard builds workforce management software for contractors. GPS-verified time tracking tied to cost codes and job budgets, feeding payroll, trusted by over 50,000 tradespeople.

This role keeps the white-glove experience for contractors we cannot afford to call every month, by running programs that reach all of them and working the accounts that need a human.

You will own retention for our mid-market and SMB customers. Larger accounts get personal coverage and renewal conversations you run yourself. Smaller ones get a program you design, with your time going to the accounts it flags as at risk. Roughly half your week is the program, half is the book.

What you will do

• Own gross revenue retention and renewal rate for your book
• Run the renewal calendar so no contract reaches its date cold, and handle the renewal conversations for larger accounts yourself
• Work a health score daily to find contractors who are slipping, and tell us where the score is wrong so we can tune it
• Use that same score to find contractors who are thriving, and turn them into testimonials, referrals and case studies
• Build and run enablement that gets contractors using features they already pay for: in-app messages, walkthroughs, webinars by trade
• Generate monthly-to-annual conversion leads out of the program
• Bring churn reasons and adoption blockers back to Product with the evidence attached

What you need

• 3+ years in customer success, renewals or account management at a B2B SaaS company, carrying a retention number
• Experience with a book measured in hundreds of accounts, not dozens
• You run your own reporting. Filtering, segmenting, exporting, and digging in when a number looks off
• Fluency in a CS or marketing automation tool such as Intercom, HubSpot or

Customer.io

. You have built sequences, set audience rules and read the results

You work with AI daily. We use Claude across the business, and you should be the kind of person who reaches for it to pull apart an export, draft a campaign, or make sense of a pile of call notes

• You notice when something is broken, like a campaign that stopped sending or a segment that quietly emptied, and you describe it clearly
• You can run a renewal conversation with an owner who is ready to cancel
• Plain communicator. Our contractors want a straight answer, not a deck

Bonus points

• Construction, field services, or another industry where the customer is not at a desk
• Basic SQL, or the appetite to pick it up
• Experience with product analytics such as Amplitude

What we offer

$80,000 base with $102,000 OTE, variable tied to retention you can influence. Fully remote anywhere in the US, with no office and no hybrid schedule. Full benefits. This is the first dedicated retention role at Workyard, so your read on the book shapes what we build next.