Head of Deployments

About the role

Customer deployments are a strategic priority at Assembled. Customers who are set up well out of the gate retain and grow at higher rates—customers who aren't, don't. You'll lead a team of 8-10 Deployment Strategists supporting contracts from $10K to $2M+, spanning small teams to large enterprises like Square, Autodesk, Hubspot, and Robinhood. The Head of Deployments owns our Deployments function—WFM onboarding and AI deployments—end to end. This is a role for someone who can run a deployment org with operating discipline from day one: playbooks, capacity planning, time-to-value benchmarks, services P&L, and a team that gets customers live fast and right. It's a substantive role for a strong operator who wants strategic and tactical work at a company at an inflection point. You'll learn directly from a seasoned CCO, and grow into more scope as the business scales.

Responsibilities

• Own Deployments end to end: technical onboarding, project management, and time-to-value for new customers across segments, including AI deployments.
• Lead and develop the Deployment Strategist team, including coaching, capacity planning, and feedback loops.
• Build the playbook: repeatable, scalable deployment processes from an unstructured, high-ambiguity starting point.
• Own the Sales-to-Deployment handoff: pre-sales support, scoping accuracy, SOW guardrails, and ensuring what's sold matches what's deliverable.
• Own the revenue number and P&L plan. Create Services packages for Deployments, enable Sales, and book $1M in Services revenue over the next 12 months.
• Benchmark and then improve time-to-value, especially for customers spending $100K+.
• Serve as the escalation point for at-risk deployments—diagnose root cause, unblock, and report status to leadership.
• Own the systems and tooling that run Deployments, from project tracking to capacity planning.
• Partner with Product and Support to close the loop on recurring implementation issues.

About You

• Strong customer-facing orientation and communication; comfortable in executive meetings and in the weeds with a deployment plan.
• Hands-on, builder's mindset—thrives creating structure and repeatability from scratch.
• People leader with strongly held principles; has managed a team of 8+ with a proven track record of success.
• Comfort with pre-sales and value framing, particularly for AI adoption / change management contexts.
• Services or professional-services leadership range: has run a P&L, priced engagements, or made build-vs-partner calls before, even if not in this exact scope yet.
• Startup experience. Consulting experience. Services experience.
• Curious, proactive, and accountable with a passion for driving outcomes for customers.

Benefits

• Generous medical, dental, and vision benefits
• Flexible time off
• Monthly credits for professional development, general wellness, Assembled customers, and commuting
• Paid parental leave
• Onsite work model with catered lunches everyday (M–F), snacks, and beverages in our SF & NY offices
• 401(k) plan enrollment

Pay

The estimated on-target earnings for the role ranges from $240,000 - $300,000, structured as an 80/20 split between base salary and variable compensation. The base pay offered may vary depending on location, job-related knowledge, skills, and experience, but the 80/20 base-to-variable split will remain consistent for the role. Stock options are provided as part of the compensation package.