Jobs at PermitFlow

Leads and grows an engineering team building new products from concept through commercial launch. Partners with product leadership to translate market hypotheses into architectures, makes build-versus-buy decisions, owns technical execution, and improves reliability, observability, and scalability. The role combines hands-on technical leadership, people management, hiring, career development, and high-ambiguity 0-to-1 product development.

Lead and grow the engineering team responsible for PermitFlow’s agentic AI infrastructure and evaluation systems. Own architecture for orchestration, model serving, reliability, latency, cost, and failure handling. Build evaluation pipelines using golden datasets, LLM-as-judge systems, human annotation, and online monitoring. Partner with product leadership to define automation quality standards, drive the technical roadmap, improve production reliability, and hire and develop AI-focused engineers.

Build and lead PermitFlow’s Product Operations organization, defining product planning, quality, launch, measurement, and customer feedback systems. Hire and develop Product Operations Managers, establish scalable operating processes, improve cross-functional execution and business metrics, and drive AI adoption across product workflows. This player-coach role partners with Product, Engineering, Design, GTM, Customer Success, Operations, and company leadership in a fast-growing startup.

Own PermitFlow’s B2B events portfolio, including industry conferences, owned events, customer gatherings, and field marketing. Manage event strategy, calendars, budgets, vendors, logistics, staffing, and execution. Drive high-value attendance, connect events to pipeline and revenue, measure performance, and report results to leadership. Partner with demand generation, product marketing, sales, customer success, and business operations while building scalable event processes and sourcing executive speaking opportunities.

Own video and photo production from concept through publication, including filming, editing, and publishing content from customer, internal, recruiting, and industry events. Create social-ready recaps, highlights, interviews, and clips; develop employee story series; coordinate event support and social calendars; and tailor content for intended audiences. The role requires strong storytelling, independent shoot management, editing expertise, organization, and the ability to deliver polished content quickly.

Lead and coach an enterprise Account Executive team while owning revenue, forecasting, pipeline execution, hiring, and account expansion. Drive complex multi-stakeholder SaaS deals exceeding $1M, build repeatable sales processes, develop ROI-based business cases, and partner with cross-functional teams to improve enterprise sales strategy and customer outcomes. Travel as needed for customer meetings, conferences, and headquarters visits.

Lead and grow a high-performing engineering team while remaining hands-on with architecture, system design, code review, and technical decisions. Own roadmap planning and delivery, build scalable and reliable infrastructure, improve observability and performance, and partner with product, design, and leadership to solve ambiguous problems. The role also involves hiring, mentoring, developing engineering culture, and ensuring systems deliver measurable customer impact.

Own analytics for Customer Success and Operations by translating ambiguous business questions into metrics, reports, dashboards, and PRDs. Partner with senior leaders, CSMs, Analytics Engineers, and Operations teams to improve retention, permit turnaround, and organizational scalability. Build self-service dashboards, develop dbt models, document analytics assets, prioritize high-impact requests, and use LLM tools to accelerate SQL, reporting, and data-model development.

Own and scale PermitFlow’s Commercial sales pod from two to seven or more AEs. Recruit, coach, and ramp enterprise sellers; build the sales playbook, forecasting, pipeline, compensation, and quota processes; lead complex multi-stakeholder deals across AEC, real estate, and commercial verticals; develop ROI-based business cases; and partner with Solutions Consulting, BDR, Customer Success, and Operations to drive land-and-expand revenue.

Lead and scale an enterprise or midmarket Customer Success team, own retention and expansion, manage executive relationships, drive adoption across multi-branch accounts, execute success strategies, partner cross-functionally, and mentor CSMs to deliver measurable outcomes.

Lead end-to-end product design for a B2B permitting platform: define strategy, ship customer- and internal-facing features, raise design craft, collaborate cross-functionally, and scale UX for workflow-heavy complexity.

Lead end-to-end product design for a workflow-heavy B2B permitting platform. Own strategy for key product surfaces, work closely with customers, engineering, sales, and marketing, set design craft standards, and deliver scalable, high-quality UX and visual solutions.

Own end-to-end recruiting for non-technical roles, develop proactive sourcing strategies, partner with leadership on hiring priorities, screen candidates, advise hiring managers, manage candidate communications, track recruiting SLAs and timelines, and report on metrics to improve hiring outcomes. The role requires independent execution in a startup or fast-paced environment and strong recruiting operations using Ashby ATS.

Own full-cycle recruiting for business and corporate roles, develop proactive sourcing strategies, partner with leadership on hiring priorities, screen candidates, advise hiring managers, manage candidate communications and recruiting timelines, and report on metrics. The role requires startup experience, strong sourcing capabilities, independent ownership, and proficiency with Ashby ATS.

Lead creation and evolution of PermitFlow's design system (Cornerstone): define components, tokens, patterns, accessibility, performance, and governance. Partner with frontend and platform engineering to ship production-ready components, create documentation and onboarding, set multi-year roadmap, mentor designers, and ensure brand cohesion across complex, AI-enabled workflows.

Lead end-to-end onboarding for strategic enterprise accounts, managing complex multi-stakeholder implementations, project plans, timelines, and cross-functional coordination to drive product adoption and time-to-value. Serve as primary customer contact, deliver training and enablement, measure onboarding success, and create scalable playbooks and processes.

Partner with the CEO as a strategic thought partner and operational extension. Lead cross-functional, high-priority projects end-to-end, hold executives accountable for execution, manage confidential executive communications, and align teams to accelerate company objectives in a fast-paced, data-driven startup.

Lead and coach a team of enterprise Account Executives to hit revenue targets, manage forecasting and pipeline, close complex $1M+ multistakeholder deals, recruit and develop sales talent, refine scalable enterprise processes, partner cross-functionally, and surface customer insights to inform GTM strategy.

The Implementation Specialist will manage onboarding and implementation for mid-market accounts, coordinate with internal teams, and lead training to drive product adoption and success for customers.

Lead and grow the Implementation team owning customer onboarding from contract signature through the first 90 days. Hire, mentor, and coach Implementation Managers; run operating cadence (1:1s, pipeline and account health reviews, post-mortems); manage escalations and at-risk launches; partner with Sales, Customer Success, and Ops; identify and close recurring launch friction via process, tooling, and playbooks.