Scaled Customer Success Manager

Workyard; Northern (KY); Hybrid; USD 80,000 - 102,000; Full time

Benefits offered by this job

Healthcare benefits

FSA

Teladoc

One Medical membership

401(k) plan

Pre-tax commuter benefits

Job summary

Workyard, a leader in contractor workforce management software, is seeking a Customer Retention Manager to own renewal and gross revenue retention for mid-market and SMB customers. You will design programs to keep accounts engaged, reach out to at-risk segments, and contribute to larger renewals with a personal touch.

You will use health scores, run renewal calendars, and collaborate with Product to remove blockers.

Qualifications

• 3+ years in customer success, renewals or account management at a B2B SaaS company with retention metrics.
• Experience managing hundreds of accounts and owning renewal/retention.
• Proficient in building and running reports with filtering and exporting.
• Fluency in a CS or marketing automation tool such as Intercom, HubSpot or Customer.io.
• Experience with AI daily; comfortable using Claude.
• Ability to drive renewal conversations with at-risk accounts.
• Clear, concise communicator for contractors.

Responsibilities

• Own gross revenue retention and renewal rate for your book.
• Run renewal calendar and handle renewals for larger accounts.
• Track health score daily and suggest improvements.
• Identify thriving contractors and turn them into testimonials.
• Build enablement to drive feature usage (in-app messages, walkthroughs, webinars).
• Generate monthly-to-annual conversion leads from the program.
• Report churn reasons and adoption blockers to Product with evidence.

Skills

Retention management

B2B SaaS

Account management

Data reporting

Intercom

HubSpot

Customer.io

AI tooling

Renewals

Communication

Tools

Amplitude

SQL

Job description

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.

Benefits

Comprehensive benefits including Aetna medical, dental, and vision coverage, Flexible Spending Accounts (FSA), Teladoc virtual care, One Medical membership, Kindbody family-building support, an Employee Assistance Program, 401(k) retirement plan through Empower, and pre-tax commuter benefits (for those based in our San Francisco office).

Equal Opportunity Employer

Workyard is an Equal Opportunity Employer and does not discriminate based on race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, genetic information, or any other protected characteristic under applicable law.

Accommodations

Workyard is committed to providing reasonable accommodations for individuals with disabilities during the hiring process. If you require assistance or accommodation, please contact us so we can support you.