Senior Manager/Director, Customer Success

About the role

PermitFlow is revolutionizing the construction sector by leveraging artificial intelligence to enhance the permitting and project management processes. We are on the lookout for an experienced leader to oversee our enterprise Customer Success team, which is dedicated to our most significant clients. This position will be in fostering customer loyalty, driving account growth, and promoting advocacy among complex client portfolios. You will be responsible for setting the vision and operational rhythm for a high-performing enterprise team, ensuring that customer outcomes are directly tied to the strategic goals of the company. The role requires a leader who is equally comfortable navigating executive boardrooms and diving into the granular details of customer workflows. You will own the end-to-end journey of our enterprise clients, translating their business objectives into successful adoption of our platform. This is a pivotal role that bridges the gap between our product offerings and the real-world needs of the construction industry. Your leadership will be the primary driver in transforming clients from users into vocal advocates.

Key facts

What you'll do

• Architect and lead the execution of a comprehensive enterprise engagement strategy that aligns with the growth objectives of PermitFlow.
• Directly manage and mentor a team of eight Enterprise Customer Success Managers, cultivating a culture of ownership, accountability, and exceptional service delivery.
• Own and optimize key enterprise metrics, including gross and net retention, expansion revenue, and contract renewal rates across multi-stakeholder environments.
• Establish and facilitate executive business reviews, ensuring that strategic value realization is consistently communicated and documented.
• Develop and maintain detailed multi-threaded relationship maps for each major account to identify influence, mitigate risk, and uncover new growth opportunities.
• Act as the primary executive sponsor and escalation path for our most strategic customers, interfacing directly with C-suite and VP-level stakeholders.
• Analyze complex customer interaction data to identify health risks and churn signals, intervening proactively to preserve and expand accounts.
• Collaborate cross-functionally with Sales, Product, and Operations to translate enterprise feedback into actionable improvements and roadmap priorities.
• Create structured implementation strategies and success plans that guide clients from onboarding through maturity, ensuring alignment with their specific operational workflows.
• Champion customer feedback and qualitative insights internally, ensuring that the voice of the enterprise customer drives strategic decision-making and product evolution.
• Produce high-impact documentation, including executive summaries, ROI analyses, and coaching materials, to elevate the standard of communication within the team.
• Identify at-risk accounts and work closely with Customer Success Managers to deploy tailored retention strategies, preserving long-term revenue streams.
• Measure and report on the team's impact on customer advocacy, ensuring that success is defined by measurable business outcomes for the client.
• Foster a data-driven culture within the enterprise team, leveraging CRM and customer success platforms to track performance and predict outcomes.
• Build and maintain strong partnerships with internal leaders to ensure the customer perspective is integrated into high-level planning and resourcing decisions.

Requirements

• A minimum of four years in a leadership capacity within Customer Success, including experience managing a team focused on retention or revenue goals.
• At least eight years of cumulative experience in Customer Success, with a strong background in the enterprise segment, managing complex accounts with multiple stakeholders.
• Demonstrated history of managing relationships with senior executives and decision-makers at large organizations, navigating C-suite-level interactions with confidence.
• Strong analytical skills, with comfort in utilizing business intelligence dashboards, customer health metrics, and translating data into actionable strategies.
• Exceptional written and verbal communication skills, evidenced by the ability to produce clear documentation, insightful analyses, and polished presentations.
• Proven experience in startup or rapidly growing environments, demonstrating adaptability, resilience, and a proactive, results-oriented mindset.
• The ability to coach and develop Customer Success Managers, fostering a culture of continuous learning and performance improvement.
• A deep understanding of the customer journey, from initial adoption through expansion and renewal, within complex enterprise sales cycles.

Nice to have

• Familiarity with AI applications in customer success or project management.
• Experience in the construction or related industries, providing a deeper understanding of client needs.
• Knowledge of customer success software tools and platforms that enhance team efficiency.
• Previous experience in developing training programs for Customer Success teams.
• A strong network within the enterprise customer success community.

Practical notes

PermitFlow provides a competitive salary and equity package, along with comprehensive benefits including 100% company-paid medical, dental, and vision coverage for employees. Additional perks include a healthcare flexible spending account (FSA), a 401(k) plan, unlimited paid time off (PTO), paid family leave, a stipend for home office setup and equipment, complimentary daily lunches and dinners in the office, and commuter benefits. We are committed to fostering a supportive and inclusive work environment that empowers our employees to thrive.