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 the company 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 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. This is the first dedicated retention role at Workyard, so your read on the book shapes what the company builds next.

Responsibilities

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

Requirements

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; Runs own reporting, including filtering, segmenting, exporting, and investigating numbers that look off; Fluency in a CS or marketing automation tool such as Intercom, HubSpot or Customer.io, including building sequences, setting audience rules and reading results; Works with AI daily (Claude used across the business) for analyzing exports, drafting campaigns, and making sense of call notes; Notices and clearly describes when something is broken, such as a campaign that stopped sending or a segment that quietly emptied; Can run a renewal conversation with an owner who is ready to cancel; Plain communicator who gives straight answers

Nice to have

Experience in 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

Benefits

Comprehensive benefits including Aetna medical, dental, and vision coverage; Flexible Spending Accounts (FSA); Teladoc virtual care; One Medical membership; Kindbody family-building support; Employee Assistance Program; 401(k) retirement plan through Empower; Pre-tax commuter benefits (for those based in the San Francisco office); Variable compensation tied to retention