Head of Customer Success

We are HCSS. For the last 40 years, we have been developing software to help construction companies streamline their operations. Based in Sugar Land, TX, our mission is helping customers achieve excellence through our proven customer-centric, end-to-end solutions and exceptionally helpful service, while providing a great life for our employees. With this mission at the core of everything we do, HCSS is a pioneer and leader in the construction software space and a consistently recognized employer.

We have earned Best Companies to Work for in Texas honors for 18 consecutive years and have been named a USA Today Top Workplace. HCSS has also been recognized by Built In as a Best Place to Work in Greater Houston and by Construction Executive for our technology innovation, reflecting our strong culture, industry leadership, and commitment to excellence.

Partnering with the CCO, you will own the execution of our Customer Success strategy through a period of rapid growth — driving retention (GRR), maturing our CS Operations/Analytics capabilities, and building a team that delivers measurable outcomes. You'll build on our reputation for excellent customer support, operating comfortably with customers, your team, and executive leadership alike, with fluency in the financial mechanics of retention (GRR, NRR, ACV, renewal economics).

• Renewals ownership and multi-product portfolio experience
• 5+ years of progressive leadership experience in Customer Success or a related customer-facing function, including experience managing people managers (not just individual contributors)
• Fluency with tools like Gainsight and Salesforce, with a track record of setting tooling strategy
• Analytically fluent, able to question and validate retention analysis, distinguish correlation from causation, and identify root-cause drivers
• Self-actualized and committed to continuous improvement in all processes and team operations
• Expert communication skills, with the ability to hold C-level customer conversations that advance the relationship and move business forward for both parties
• Strong SaaS business acumen, decisive execution, and cross-functional collaboration skills
• Financially literate, comfortable with budget planning, GRR, and renewal economics
• Proven experience in enterprise B2B SaaS, where product adoption is driven top-down. Understands how to navigate complex, multi-stakeholder environments and drive utilization through organizational change management rather than individual end-user (Product-Led Growth) motions

• 2+ years leading a $250M+ SaaS Customer Success organization
• MBA or advanced business degree, or an industry-recognized Customer Success credential (e.g., Certified Customer Success Manager (CCSM) or Gainsight Certified Administrator)

• Translate the CCO's vision into strategy and initiatives, ensuring the organization is set up correctly to execute and drive results
• Design a team structure that can absorb fast growth across a multi-product portfolio and complex, multi-stakeholder B2B accounts.
• Build execution plans that turn strategy into real operational change at scale.
• Review and adjust plans as the business evolves, staying ahead of change rather than reacting to it.
• Maintain a direct pulse on the customer base by regularly connecting with them to deeply understand their workflows, pain points, and business realities, using these frontline insights to inform and validate your strategic execution.

• Evolve our Customer Success practices as we scale, focusing the team on high-value work: achieving customer goals and expanding the value of our products and services to drive customer lifetime value.
• Define, model, and reinforce a department-wide culture that is customer-obsessed, outcome-focused, collaborative, and accountable.
• Establish standard practices, playbooks, and workflows with the CS Leadership team to proactively anticipate and address emerging customer needs.
• Strengthen account transitions and the end-to-end customer journey, ensuring clear ownership, seamless transitions, and early visibility into risk.
• Set the tooling strategy for our broader technology stack. Proactively evaluate and implement new technologies to drive efficiency, scalability, and predictive capabilities that anticipate emerging customer needs.

• Mature our health scoring, retention forecasting, and root-cause reporting, giving the business a credible view of account health and potential risks.
• Lead variance analysis on GRR/renewal performance and communicate it credibly to stakeholders, explaining what's driving gaps, not just reporting the number.
• Turn department performance into a clear, visual story for leadership with the data and the narrative behind it.

• Partner in annual budget planning and informing renewal forecast assumptions.
• Build a network of customer advocates and…