Head of Professional Services (Implementation & Delivery)

About GoodTime

GoodTime is the leader in complex interview scheduling automation for enterprise talent teams. Built for scale, our platform handles the complexity others can’t — automating every type of interview, from multi-day panels across time zones to high-volume hiring events, with unmatched speed and precision. 

Behind every seamless schedule is our digital workforce of AI agents that eliminate delays, surface insights, and keep hiring teams perfectly in sync. Leaders at companies like Databricks, Aon, HubSpot, and HelloFresh trust GoodTime to orchestrate smarter, faster, people-first hiring experiences for their candidates, interviewers, and talent teams.

We operate with a culture of autonomy, accountability, and collaboration. People here don’t wait for permission — they solve problems, own outcomes, and work closely with customers to get it right.

About the Role

We are looking for a Head of Professional Services to build and run the delivery engine behind our customers’ success.

You will personally own customer outcomes when things are unclear, messy, or high-stakes — and then build the systems so the company no longer depends on heroics.

You will lead implementations, manage escalations, design delivery architecture, and develop a team that can support enterprise scale while maintaining a high-trust customer experience.

This role collaborates closely across the whole company -- Sales, Customer Success, Product, and Engineering.

Why This Role Matters

Professional Services shapes how customers experience the product in reality — not in demos.

This role determines whether the company scales smoothly or accumulates operational drag as it grows.

You will build the operational backbone that turns new customers into long-term partners.

What You’ll Own

Delivery Execution

• Own successful onboarding and expansion delivery across all customers
• Directly step into complex or escalated implementations
• Establish clear implementation methodology and standards
• Drive predictable time-to-value and adoption outcomes
• Create recovery plans for at-risk accounts

Customer Leadership

• Lead executive-level escalation conversations
• Restore confidence when projects go off track
• Translate technical limitations into business decisions customers can trust
• Balance customer advocacy with company sustainability

Team & Partner Management

• Hire, coach, and develop implementation managers and solutions architects
• Define what good looks like for delivery roles
• Manage implementation partners and hold them accountable to standards
• Build a culture of ownership, not ticket routing

Systems & Scale

• Design processes that scale beyond individuals
• Introduce segmentation, playbooks, and delivery tiers
• Create an escalation governance model
• Reduce firefighting over time

Cross-Functional Leadership

• Partner with Product to surface recurring friction
• Help Sales set realistic expectations before deals close
• Work with CS on handoff and expansion readiness
• Improve feedback loops across the customer lifecycle

What Success Looks Like

Within the first 6–12 months, you will:

• Stabilize delivery quality across implementations
• Reduce escalations and recovery projects
• Establish predictable onboarding timelines
• Build a team that owns outcomes instead of coordinating tasks
• Enable partners to deliver consistently under your framework
• Earn trust from enterprise customers and internal teams

We’re Likely a Fit If You

• Have led Professional Services, Implementation, or Delivery in a B2B SaaS company
• Have personally run complex enterprise implementations
• Are comfortable being the escalation point with senior customer stakeholders
• Use data to diagnose operational problems
• Prefer solving problems directly before delegating them
• Can operate in ambiguity and build structure over time
• Can balance speed, customer experience, and company constraints

This Role May Not Be the Right Fit If You

• Prefer staying primarily at the strategic rather than engaging directly with customers and day-to-day situations
• Avoid stepping into difficult customer conversations
• Default to adding headcount before fixing systems
• Rely heavily on other teams to resolve delivery issues
• Need a highly structured environment or fully built process rather than making fast decisions and iterating quickly
• Dislike frequent collaboration across functions
• Prefer predictable, low-change environments

Commitment to you

The more diverse and inclusive the workplace, the more our product, community, and company can flourish. As a prospective teammate, we don’t expect you to “check” every box here. If you believe in the vision and values at GoodTime, please apply! We’re proud to support and be an ally to the BIPOC community, women, veterans, and those recovering from the various effects of the pandemic. 

Benefits

• Remote first culture, with fully paid annual company get togethers for ALL teammates
• Health, Dental, and Short-term Disability plans, with generous employer contribution
• Flexible time off 
• 8 week Parental Leave (including adoption placement)
• $500 home office reimbursement
• Up to $500 towards self-selected learning and development
• Pre-IPO Stock Options

Travel: ~20-30%

Remote in United States or Canada

Please Note: No 3rd Party Agency/Recruiters will be considered.