Head of Customer Success

Heavy Construction Systems Specialists, Inc.; Sugar Land (TX); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Flexible hybrid schedule

Medical, dental, and vision coverage

Paid holidays, sick days, and personal

Employee Resource Groups (ERGs)

On-site amenities including basketball

Dog-friendly campus

401(k) with 5% company match

Professional development support

Wellness programs

Job summary

Heavy Construction Systems Specialists, Inc. in Sugar Land, TX, is seeking a Director of Customer Success to lead strategy, expand multi-product CS operations, and partner with executive leadership to improve retention and lifetime value.

You will build a scalable CS organization, establish playbooks, and collaborate with Implementation, Product, Marketing to drive adoption and customer outcomes. The role requires strong SaaS leadership and enterprise B2B experience.

Qualifications

• 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

Responsibilities

• 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.

Skills

Leadership

Renewals ownership

SaaS business acumen

Cross-functional collaboration

Executive communication

Data-driven decision making

Budget planning

Customer success strategy

Enterprise B2B SaaS

Root-cause analysis

Education

MBA or advanced business degree

CCSM or Gainsight Certified Administrator

Tools

Gainsight

Salesforce

Job description

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.

WHO WE NEED:

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).

Qualifications:

• 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

Preferred Qualifications:

• 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)

Role Responsibilities:

Strategic Execution & Scale

• 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.

Center of Excellence

• 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.

Data-Driven Insight

• 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.

Cross-Functional Collaboration & Strategic Relationships

• Partner in annual budget planning and informing renewal forecast assumptions.
• Build a network of customer advocates and resolve cross-departmental friction independently.
• Drive Net Dollar Retention (NRR) by identifying opportunities for expansion where our products deliver tremendous value to customers, and by actively generating and passing high-quality leads to the Sales department.
• Partner with Implementation and Product Management to turn customer signals into action through a standing feedback loop.
• Serve as the ultimate escalation point for the broader Customer Success team, proposing end-to-end resolutions structured for mutual benefit.
• Engage strategically with various departments to drive customer advocacy programs such as Customer Advisory Boards (CABs) and HCSS Champions Program.
• Collaborate with Marketing to build a systematic approach for cultivating referenceable customers, ensuring the CS team consistently identifies and flags high-value outcomes to be developed into public case studies and success stories

Key Performance Indicators:

• As the Director of Customer Success, your impact will be measured by a combination of financial outcomes, operational maturity, and customer advocacy. Your primary KPIs include:
• Renewal & Churn: Gross Retention Rate (GRR) and Churn ($ and %) against plan, with clear visibility of at‑risk ARR and mitigation status.
• Expansion / Qualified Leads: Expansion (NRR) contributed or influenced by the team.
• Top-Down Adoption & Advocacy: Successful organizational change management milestones, and the volume of referenceable accounts generated for Marketing case studies.
• Coverage Metrics: C‑Suite Relationships, High‑Risk Accounts, Success Plan Reviews, EBRs, Value Unlock Sessions, health score coverage, and updates.

Travel Requirements:

Limited travel. Required to be in office Tues/Wed

BENEFITS & PERKS:

Part of our mission is to provide a great life for our employees. We believe that when our people are happy, they do their best work. Some of the benefits and perks we offer include:

• Flexible hybrid schedule
• Medical, dental, and vision coverage with company-paid and employee-paid options
• Paid holidays, sick days, and personal time off
• Employee Resource Groups (ERGs) that foster connection and inclusion
• On-site amenities including a covered basketball court, soccer field, track, pickleball/tennis courts, gym, etc.
• Dog-friendly campus and WiFi-accessible courtyards
• 401(k) with a 5% company match
• Coverage for employee professional development and wellness
• And more!