Director of Technology & AI

At Baysora, we partner with boutique tax and accounting firms to protect what makes them unique while fueling their next chapter. Backed by patient family capital, we take a long-term approach that prioritizes people, culture, and client service. Joining our team means being part of a network that values autonomy, invests in growth, and creates clear pathways for future leaders.

Baysora is building a modern, technology-enabled operating model across a growing group of tax, accounting, and financial services firms. We are hiring a Director of Digital Transformation & AI to drive measurable productivity gains by inserting technology into everyday workflows at Hold Co and across partner firms - using AI, automation, integrations, and practical process redesign.

This is a builder-minded role, but not a "code all day" role. You will be hands-on in implementation: configuring and integrating tools, creating automated workflows, and occasionally building lightweight functionality on top of existing platforms (e.g., scripts, small services, internal utilities, prompts/agents, and glue code). You will also lead the discovery and prioritization of the highest ROI opportunities and ensure adoption through training and documentation.

This role sits at the intersection of technology, operations, and change management. Success is defined by repeatable impact: implemented workflows and tools that are adopted, measured, and scaled across multiple firms.

• Flexible work environment (Hybrid)
• Medical, Dental, and Vision benefits package
• 401(k) with employer match
• Unlimited PTO
• A supportive culture to allow you to live a fulfilling, happy, and impactful life

• Holdco efficiency: deeply learn Baysora's operating rhythms and continuously remove low-ROI work through automation and better tooling.
• Practical AI: deliver real productivity improvements by embedding AI into daily workflows with appropriate safeguards and quality checks.
• OpCo enablement: partner with firm leaders to modernize their workflows in ways that fit their tools, client commitments, and compliance realities. Then package what works into repeatable playbooks.

• Map end-to-end workflows and identify bottlenecks, rework, and handoffs that can be automated or simplified.
• Implement automation across everyday systems (docs, spreadsheets, email, calendars, ticketing/project tools) and line-of-business platforms.
• Create lightweight integrations and utilities when off-the-shelf tooling falls short (scripts, webhooks, small apps, glue services).
• Create a simple internal "automation backlog" with ROI estimates; deliver in short cycles and report results.
• Stand up repeatable patterns for document generation, data collection/intake, reporting, and internal support.
• Establish AI governance basics (data handling, confidentiality, acceptable use, review standards) appropriate for a professional services environment.
• Partner with firm leaders to understand their workflows, constraints, and tools (seasonality, client deadlines, compliance considerations).
• Identify and implement practical improvements (tool configuration, workflow redesign, automation, and AI-enabled support) tailored to each firm's operations.
• Translate successful initiatives into repeatable playbooks ("what to do, how to do it, how to measure it") so other firms can adopt quickly.
• Support change management: rollout plans, training, documentation, and ongoing iteration based on feedback and metrics.

• 5+ years building and implementing technology solutions that improve operations (automation, integrations, internal tools, analytics, or product).
• Hands-on implementation ability: you can build and ship practical workflows, automation, and lightweight tooling.
• Experience operationalizing AI in real workflows (not just experimentation) with attention to quality, safety, and adoption.
• Ability to translate messy operational pain into solutions; comfortable working with leaders and front-line teams.
• Strong judgment and prioritization: consistent focus on measurable ROI and change management.

• Experience in or adjacent to accounting/tax/financial operations (or building solutions for professional services).
• Experience working in a multi-entity environment (holding company / roll-up / PE-backed platform) and scaling playbooks across teams.
• Ability to work across common accounting-firm and back-office systems (document management, practice management, time & billing, tax/audit tools).
• Competence with data (SQL/spreadsheets), APIs, and basic security/privacy practices.