Director of Development & Automation
About the Role
Reports to: CTO
We're looking for a Director to take ownership of Digacore's Development & Automation (DNA) team - a capable group of developers, data, product, and AI specialists working across three streams: AI services for clients, internal data and reporting, and a client-facing software product. The direction is set; now it needs a leader to turn it into structure, consistency, and results, so the CTO can step back from the day-to-day.
You'll start by getting to know the team and what's in flight, then put the foundation in place - SOPs, guidelines, a delivery cadence, and KPIs that give leadership a clear view of where things stand - and grow the team as the work demands. You're comfortable rolling up your sleeves to unblock a build or prove out a solution, but your impact comes from leading through others, not writing the code yourself.
What You'll Do
- Lead the existing team: learn each person's strengths, set clear ownership, and manage each one the way they need - including senior specialists who are deeper than you in their own domains
- Set the standards: write and roll out SOPs and guidelines for how the team works - intake, prioritization, delivery, documentation, and handoffs - starting with our repeatable client AI Services processes
- Own the KPIs: define and track the metrics that prove impact (time to deploy, delivery against dates, time saved, adoption, ROI) and give the CTO a clear monthly view of what's on track and what isn't
- Run the team's weekly delivery cadence so every initiative has an owner, a priority, a next step - and status is visible at any point without chasing people down
- Own the roadmap across all three streams - when urgent asks compete, decide what comes first, what waits, and what doesn't happen, and reset expectations with stakeholders
- Take ownership of client AI engagements - assessment, setup, training, and custom builds - so they move from signed to live quickly and run without escalating to the CTO
- Oversee product releases with the Product Owner and developers - pressure-test estimates, surface risk early, and hold to commitments
- Back the internal data and reporting work - the data warehouse and leadership scorecard, including AI Services results - so leadership gets numbers it trusts
- Be the escalation point on client issues - including security, compliance, and data privacy questions - and prepare the team to handle them well
- Partner with leadership and department heads to identify manual work and friction, and turn it into automation and AI solutions
- Grow the team when needed - identify gaps, define new roles, and hire and onboard as the function scales
- Own tooling and vendor decisions, budget input, and capacity planning for the function
What Success Looks Like in Year One
- Every team member known with clear ownership, and every initiative inventoried with an owner, priority, and next step
- A weekly delivery cadence running, and a monthly KPI report the CTO can read in two minutes
- Core SOPs written and followed, starting with client AI deployment
- The CTO out of routine client engagements, with client builds moving from signed to live on a fast, predictable timeline
- Shipped wins with documented ROI, and a clear view of where the team needs to grow next
What You Bring
- Proven leadership: 7+ years in automation, development, data, or technical operations, including 3+ years leading a technical team with direct reports - coaching, accountability, and running a delivery cadence
- You've built the playbook: a track record of putting SOPs, operating rhythms, and KPIs in place for a team that didn't have them - and getting people to actually follow them
- Experience leading people more technical than you - you set outcomes and check progress without micromanaging
- Shipped AI, automation, or software that moved a measurable number - not pilots and slide decks
- Strong technical grounding in the Microsoft stack (M365/Azure, Power Platform, Power BI), APIs, and integrations - enough to unblock, review, and build when needed
- Comfortable in client-facing work, including tough conversations around data, security, and compliance
- Strong business translation - you turn "we need X" from non-technical stakeholders into a delivered solution
- Thrives in a lean, fast-moving environment - candidates who need heavy corporate structure won't be the right fit
Nice to Have
- MSP, SaaS, or multi-client service experience
- Background in software product delivery or data/BI leadership
Compensation:
$150,000-$180,000 Annually (depending on experience)
Perks & Benefits
- Nationwide medical, dental, life, and LTD insurance (we cover LTD + life 100%)
- Generous PTO + Mental Health Days
- 401(k) with company match
- HSA & FSA options
- Paid training & certification assistance
- $500 sign-on bonus
- Quarterly team events and career coaching
