VP, Product Support

CentralSquare Technologies is Hero-Grade. As the trusted provider of public sector software in North America, more than 8,000 agencies rely on our comprehensive, cloud-based platform to manage critical operations – from dispatch to records, permitting to payroll. We serve with purpose and stand together with our heroes, committed to supporting the public sector with software built for impact. 

Vice President, Product Support

Role Profile:

The Vice President, Product Support leads CentralSquare's frontline customer support organization: the people who resolve issues, manage escalations, and represent CentralSquare directly to the agencies and public servants we serve. This is a customer-facing leadership role.

Support at CentralSquare is undergoing significant change as AI-assisted deflection, agent-assist tools, and automated triage absorb a growing share of case volume. This VP will partner closely with the Customer Support Operations and IT teams as that work rolls out, translating AI-driven change into day-to-day support operations and keeping the organization customer-first, well-run, and well-led throughout the transition.

The right candidate has led a support organization through this kind of change before: someone who is fluent enough in AI-assisted support tools to partner effectively with Customer Support Operations and IT, redesign workflows, and guide staff through new roles.

What You’ll Enjoy:

• Full benefits package including medical, dental, and 401k plans
• Paid holidays and Open Paid Time Off (PTO) policy to ensure a solid work/life balance
• Paid time off to volunteer during company hours for qualifying nonprofit organizations
• Comprehensive parental leave, adoption assistance, and pet insurance programs
• Tuition reimbursement for approved courses
• Exposure and growth opportunities within CentralSquare, and across the Vista and Bain, our private equity partners, portfolio

What You’ll Do:

Lead the Support Organization

• Own day-to-day leadership of the Product Support organization across Public Administration and Public Safety and Justice product lines, including hiring, coaching, performance management, and career development for agents and frontline managers.
• Build a culture of accountability, ownership, and continuous improvement, and ensure the organization's structure and staffing model keep pace with changing case volume and channel mix.
• Develop job descriptions and an accountability model that objectively measures performance across the organization and builds the talent bench.
• Own the organization's cost structure, achieving and maintaining support costs at 3% of ARR while balancing overtime against full-time staffing levels.
• Improve standard customer communications and internal communications that keep the organization informed of ongoing functional improvements.

Partner on AI-Assisted Transformation

• Partner closely with the Customer Support Operations and IT teams on the rollout of AI-assisted deflection, agent-assist, and automated triage tools into daily support operations.
• Lead the people side of that transition: redesign agent workflows and role definitions as automation absorbs routine volume, and manage the reskilling and career-pathing of existing staff into higher-value roles such as escalation specialists, knowledge contributors, and quality reviewers.
• Bring working fluency with AI-assisted support tools and deflection concepts (net versus gross deflection, containment, AI-assisted resolution rate) to these conversations, so the partnership with Customer Support Operations and IT is a genuine two-way exchange.
• Flag where automation is changing customer experience or agent workload in ways that need attention, and hold the line on customer satisfaction and quality as volume shifts.

Own the Operational Backbone

• Own the Salesforce Service Cloud case lifecycle for the support organization: case management, routing, escalation workflows, and reporting.
• Partner closely with Workforce Management on forecasting, scheduling, and capacity planning, accounting for combined human and AI-assisted workload as deflection changes contact volume by channel.
• Partner closely with the Knowledge and Quality Specialist function to keep the knowledge base accurate, current, and structured in a way that supports both agents and AI-assisted deflection.
• Design an account ownership function and process to reduce friction across the customer base, and develop a support strategy for Enterprise Accounts that leverages the current managed services model.
• Define and monitor KPIs and service-level standards, including case volume, first contact close, customer satisfaction, escalation rate, MTTR against committed SLAs, case backlog (target: less than 2x daily incoming volume), and agent productivity (target: 8 cases per agent per day), and report performance against targets to senior leadership.

Drive Escalation Management and Product Feedback

• Own the escalation management process end to end, ensuring timely resolution of complex or sensitive customer issues.
• Partner with Product and Engineering on root cause analysis, feeding recurring support themes back into the product roadmap and tracking whether resolved issues reduce future case volume.
• Maintain a working understanding of CentralSquare's core software platforms sufficient to guide troubleshooting, escalation triage, and customer conversations.

What You’ll Need:

• 10+ years of experience in a technical or product support environment, with 5+ years in a senior leadership role overseeing support teams or organizations.
• Direct experience leading a customer-facing support organization through an AI-assisted transformation, such as chatbot or virtual agent deployment, automated triage, or deflection technology, including the workforce and role-redesign side of that change, ideally in partnership with a dedicated support operations or IT team.
• Strong hands-on experience with Salesforce Service Cloud for case management, routing, and reporting.
• Experience partnering with a Workforce Management function on forecasting, scheduling, and capacity planning.
• Experience partnering with a Knowledge Management or Knowledge Specialist function on content strategy and knowledge base quality.
• Track record of managing a support cost structure against a percent-of-revenue target, including productivity and backlog goals, and designing account ownership or key account programs that reduce customer friction.
• Bachelor's degree in business administration or a related field, or equivalent professional experience; advanced degree preferred.
• Exceptional communication skills, including the ability to present to senior leaders, customers, and external partners.

Preferred

• Experience in government, public safety, or another regulated industry.
• Salesforce Service Cloud or AI Associate certification.
• Knowledge-Centered Service (KCS) certification or equivalent knowledge management methodology experience.
• Experience operating in a private equity-backed environment with board-level performance reporting.

Who You’ll Work With:

The VP, Product Support works hand in hand with the Customer Support Operations and IT teams on AI-assisted deflection and automation. The strongest candidates have led a support organization through this kind of change themselves, and bring both people leadership and enough AI fluency to be a real partner in that work

CentralSquare Technologies: Where Mission Meets Innovation

CentralSquare Technologies is proud to be an Equal Opportunity Employer. We are committed to fostering a workplace that is inclusive, respectful, and free from discrimination—where all individuals are valued, supported, and provided equal opportunity to succeed.

We place a strong emphasis on supporting military veterans and their spouses and recognize the leadership, discipline, resilience, and mission-oriented mindset they bring to the workforce. The skills developed through military service—such as accountability, teamwork, adaptability, and the ability to perform under pressure—are highly valued at CentralSquare and directly contribute to our success.

In addition to our commitment to veterans, CentralSquare Technologies welcomes and encourages applicants from all backgrounds. We are committed to equal employment opportunity for all qualified individuals, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, disability, veteran status, or any other characteristic protected by applicable federal, state, or local law.

Our employees reflect a wide range of experiences, perspectives, and identities, and this diversity strengthens our ability to innovate and serve the public sector, whether through our public safety or public administration businesses. Through our technology, we support public servants and the communities they serve, and we believe our workforce should reflect those communities as well.

If you are seeking an opportunity to contribute to meaningful work that impacts communities nationwide—whether continuing a legacy of service or beginning a new chapter—CentralSquare Technologies invites you to apply.

Your next mission starts here.