Head of Customer Success

About the Company:

ArcSite is the leading mobile sketching and drawing-based takeoff and estimating solution, trusted by designers, field sales teams, technicians, and inspectors. Our intuitive platform empowers users to create professional drawings on any device - without the steep learning curve of traditional CAD software - helping businesses save time, generate quotes faster, and close deals more efficiently.

We’re a remote-first team with a strong sense of community, driven by growth, collaboration, and our core values: start with the customer, constantly improve, take risks, operate with transparency, and own it. At ArcSite, every team member has the opportunity to grow their career while making an impact, shaping the future of design, and living these values in everything we do.

About the Role:

The Head of Customer Success is a key leadership role responsible for ensuring customers achieve meaningful and lasting value with ArcSite. Reporting directly to the VP of Operations, this leader oversees four core functions of the customer lifecycle:

• Enterprise Implementation
• SMB Implementation
• Customer Support
• Payments Platform Support

This role requires someone who is both a strategic thinker and a hands-on operator. You should be just as comfortable developing scalable processes and programs as you are jumping into major customer escalations or supporting team members through complex issues. The ideal candidate is scrappy, proactive, and ready to build-from systems that improve onboarding to initiatives that strengthen adoption and reduce churn.

In this role, you’ll work cross-functionally with Product, Engineering and Sales to continuously improve the customer journey, refine internal workflows, and ensure every customer has a strong, supported experience with ArcSite.

Key Responsibilities:

• Lead, mentor, and develop the Enterprise Implementation, SMB Implementation, Customer Support, and Payments teams.
• Build a high-performing, customer-obsessed organization with clear goals, processes, and accountability.
• Act as an escalation point for high-impact or complex customer issues, guiding both strategy and hands-on resolution.
• Improve reactive churn by developing systems for earlier risk detection, better customer communication, and stronger value delivery.
• Partner closely with Product and Engineering to advocate for customer needs, influence roadmaps, and translate customer feedback into actionable insights.
• Standardize and improve onboarding and implementation processes across customer segments.
• Oversee performance metrics, team KPIs, and customer health reporting.
• Collaborate with Sales to ensure smooth handoffs, strong expectations setting, and long-term customer success.
• Identify, design, and launch new programs and initiatives that increase product adoption, reduce churn, and improve customer retention.
• Ensure the Payments customer segment receives world-class support and that issues related to payment processing or workflows are quickly addressed.
• Develop repeatable processes, playbooks, and frameworks for scalability as ArcSite continues to grow.

Requirements

• 8-10+ years of experience in Customer Success, Implementation, or Customer Support, including leadership of multi-functional teams.
• Proven ability to manage a large book of customers across SMB and Enterprise, ideally within a SaaS or technical environment.
• Experience overseeing customer onboarding/implementation and support functions.
• Demonstrated success reducing churn and improving customer retention.
• Hands-on leadership style - comfortable joining calls, helping resolve escalations, and working directly with customers when needed.
• Strong problem-solving skills and the ability to design and execute improvement initiatives from idea to rollout.
• Experience working cross-functionally with Product, Engineering, and Sales.
• Excellent communication, coaching, and stakeholder management skills.
• Process-oriented but scrappy; able to build structure where needed without slowing the team down.
• Ability to thrive in a fast-paced, remote-first startup environment.

Benefits

• Fully remote
• Unlimited PTO
• Medical, dental, and vision insurance
• 401K match
• $75 monthly wellness stipend

ArcSite is an equal opportunity employer and fosters an inclusive environment. We do not discriminate based on gender, race, ethnicity, orientation, creed, or other traits. We welcome people from diverse backgrounds and perspectives to apply to our positions.