Head of Solutions

Pylon Solutions Leader

Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters. Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself. We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List.

The Role

We're hiring our first dedicated Solutions leader. This person will own the technical customer journey end-to-end: from pre-sales solution design to implementation, deployment, and long-term customer success. You'll build the function, define the playbooks, and set the standard for how technical customer-facing work gets done at our company. This is a player-coach role. We're looking for someone who can personally lead strategic deployments, run complex customer engagements, and build the systems, processes, and team that allow us to scale.

What You'll Do

Build the Solutions Function

• Define and own the operating model for Solutions.
• Build the playbooks, processes, and tooling that allow us to scale customer deployments.
• Establish clear ownership and interfaces across Sales Engineering, Implementation, Forward Deployed Engineering, and Professional Services.
• Create repeatable systems that reduce deployment time while improving customer outcomes.

Set the Standard

• Personally lead high-impact customer engagements, implementations, and technical escalations.
• Establish the gold standard for customer communication, project management, and technical execution.
• Turn your own best practices into repeatable playbooks for the team.
• Be the leader who can jump into any customer situation and help move it forward.

Build and Lead the Team

• Recruit, hire, and develop world-class Solutions talent.
• Coach Sales Engineers, Implementation Engineers, and Forward Deployed/Solutions Engineers.
• Create clear career paths and performance expectations across the function.
• Scale the organization without sacrificing quality.

Be the Bridge Across the Company

• Partner closely with Sales, Product, Engineering, and Customer Success.
• Bring customer feedback directly into product and engineering discussions.
• Help shape how the company approaches deployments, integrations, and technical partnerships.
• Act as the connective tissue between customers and internal teams.

What You've Done

• Built or scaled a Solutions, Solutions Engineering, Implementation, Customer Engineering, or Professional Services function at a B2B software company.
• Personally ran demos, implementations, integrations, migrations, or deployments before becoming a manager.
• Hired and developed customer-facing technical talent rather than inheriting an existing organization.
• Built processes and playbooks that allowed a team to scale.
• Thrived in ambiguous environments where the right answer did not already exist.

This Role Might Not Be For You If

• You want to manage people more than you want to do the work.
• You prefer operating within established processes rather than creating them.
• You are looking for a narrowly defined function with clear boundaries.
• You want to apply the same playbook you've used before without adapting it to a new category.
• You prefer remote or hybrid work. This role is based in San Francisco alongside the rest of the Solutions team.

Our perks

• Commuter benefits
• Parental leave
• 14 company holidays + unlimited PTO
• Annual offsite
• Lunch, dinner, and snacks at the office
• Fitness stipend

More about Pylon

Funding: Series B led by a16z and BCV ($51M total raised)

Founders: Advith Chelikani, Robert Eng, and Marty Kausas

Team: Currently 100+ and growing!