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Software Engineering Manager

Leonidas CaldwellYour Next Engineering Manager.

I'm a hands-on engineering leader with 10+ years in enterprise software. I led the teams and core platforms behind Rocket Mortgage's record run, at up to 13,500 transactions a day, trained and placed 100+ engineers at Microsoft and built a digital agency to continue to drive innovative products and technology.

Based in
Detroit, MI
Work style
Remote, hybrid, or on-site
Relocation
Open to it for the right role
Availability
Available now w/ 2-week notice
Evidence

The numbers behind the claim.

13.5Ktransactions / dayCore platforms scaled ~4× while I led them
1.1Mclosings in 2021A record year my team's automation unblocked
6teams orchestratedDepartment-wide epic, decrease delivery time in half
3team turnaroundsFrom low trust to model team, three times
100%of reports exceedingPlus the department's only “Rockstar” rating
100+engineers placedMicrosoft SWE, PM and TPM hires I trained and coached
Signature story

The project that kept a record year from breaking.

Escrow Audit Automation at Rocket Close: from a high-priority, high-impact feature into a six-team epic, delivered in half the estimated time and during the busiest stretch in the company's history.

In 2020, as Covid-19 cause unprecedented disruptions, the Fed cut interest rates when most analysts expected a hike. We had recently cut our headcount believing rates would rise. Our parent organization, Rocket Mortgage, relentless captured martet share from institutions who were not yet optimized for remote work. Escrow audit became the bottleneck putting client SLAs at risk.

When I initally asked to lead the feature, I was turned down. Two weeks before the new quarter, the feature was clearly drifting: the architects were overcommitted, and no one in the working sessions could speak to a plan to prioritize and execute the feature. We were stuck, the anticipated delivery was delayed to the end of the following quarter. I didn't escalate loudly. I paired with a senior engineer who was working toward architect, spent two weeks with the architecture group, and came back with a plan that addressed architectural tech debt, orchestrated AI and logical systems, and laid the foundation for upskilling our senior and mid-level engineers. Leadership handed the epic to my team.

With a sr engineer and an architect and former team member, co-designed a technical game plan that broke the epic into individual shipable components that matched to the capabilities of each team across our department. I reserved my team to do the bulk of the engineering and handle testing and integrating all the components. Together we built an orchestrator that moved each document package from scanning through document formating, indexing, OCR, ML classification, ML document bundling, ML extraction and ML signature detection, then back into the legacy core, with monitoring at every step. My teams' engineers led their counterparts on every other team. I introduced cross-team meetings where I met with our senior engineers to ensure proper communication and alignment. While most engineers were opposed to more meeting, I ensured each meeting was brief and impactful, gathering praise and cheer from the engineers on the value of the Senior Touchbases.

The result
  • Shipped in one quarter against a two-quarter estimate
  • Removed the audit bottleneck behind a record 1.1M closings and Rocket Mortgage's $351B year
  • Became the department's template for cross-team epics
  • Started the year with two engineers near a PIP and ended it with every report exceeding expectations, plus the department's only “Rockstar” rating, approved unanimously by the VP, director and peer managers
Pattern, not luck

Every team I inherited started with a problem.

Team 1 · Post-Funding & Signing Services

“The team where fun goes to die.”

This was a green team with eroded business trust, missed commitments, and directors with strong opinions in every working session. I reset expectations, rebuilt the stakeholder relationship, matched people to their strengths and wrote code alongside them to change the culture and impact of the team. We shipped two automation projects that had sat on the wish list for three-plus years, both on time or early. We projected approximately 20% of volume automated and captured over 30% upon release.

Team 2 · Tasking platform, the company's top priority

Senior engineers who had never hit a date.

This team was highly technical but had gone two years without meeting a commitment. They didn't need another coder. They needed a translator, a shield, an advocate and leader to communicate a unified vision and plan. I cut their meeting load, organized the work, secured buy-in across teams and cleared roadblocks. In my first quarter we delivered two of three features, the team's first kept commitments ever. From then on not only did we we finished our own features on-time, we helped other teams across the department finish theirs.

Team 3 · Documents platform

Day one: a security incident.

I inherited the documents platform the same week a just-launched feature surfaced a security incident, and I heard about it from my product owner on the first morning of our quarterly planning week. Without much help from the original builders, we triaged, found the root causes and remediated by the end of the week. We also implemented additional security measures to prevent similar incidents in the future. That same team then led the six-team audit automation. By 2021 my teams owned about a third of the company's products.

How I lead

Clear on Priorities. Calm in Chaos.

01

Mission → priorities

Every team needs clear mission, vision and purpose(MVP), values, priorities, roadmap and documentation.

02

Gaps and greats

Using scrum data, conversation and observation. I identify and fill the critical gaps, then align strengths to advance the company's priorities.

03

Fill the Gaps

As a hands-on leader, I adjust to what the team needs. I insert myself to fill the team's resource gaps.

04

Earn the Right to Innovate

New team? Step 1: Stabilize the core, Step 2: Earn the stakeholder trust, and Step 3: explore ways to amaze your customers, clients and stakeholders.

05

Clarity is Respect

Communicate problems clearly, invite disagreement, establish new systems of impact, then help people reach them.

My first 90 days on your team

Days 1–30Discover
  • 1:1s with every engineer and key stakeholder
  • Build the main systems locally and walk the architecture
  • Map the roadmap, backlog, tech debt and top risks
Days 31–60Align
  • Team mission, working agreements and definition of done
  • Agree on delivery, quality and reliability metrics
  • Ship an early, visible win
Days 61–90Accelerate
  • Goals tied to measurable business impact
  • A growth plan for every engineer
  • Attack the highest-leverage tech debt
Career in brief

A decade of scale, in brief.

  • B.A. Mathematics, Kalamazoo College
  • AWS Cloud Practitioner
  • SAFe Scrum Master · Certified Scrum Master
  • Next-Gen Advisory Board, First Independence Bank
  • Board Vice-Chair & Treasurer, Bradford Academy (~$20M budget)
  1. 2022 – Now
    Consultant & Software Engineering LeadFlintstone LLC

    I deliver web apps, API integrations and workflow automation from discovery to launch, and advise client leadership on technology strategy. Clients include First Independence Bank, where I'm leading the website redesign.

  2. 2022 – 2025
    Global Software Engineering Instructor & ConsultantMicrosoft

    I designed enterprise engineering programs in cloud, AI, security and full-stack development with Azure, M365 and GitHub leaders. I ran classrooms as agile product teams, and mentored and placed 100+ new hires.

  3. 2017 – 2022
    Software Engineering Team Leader · Core PlatformsRocket Close (fka Amrock)

    I led up to two teams and nine cross-functional reports across escrow, audit, documents, payments, closings and accounting. Over that time the platforms scaled from ~3,500 to ~13,500 transactions a day.

  4. 2015 – 2017
    Software Quality EngineerRocket Close (fka Title Source)

    I built 600+ automated UI and integration tests for a .NET/WPF core platform, introduced integration testing to the Title channel, and mentored new QEs.

  5. 2012 – 2015
    Student Life CoordinatorInternational Preparatory Academy

    I built the systems behind a turnaround school's culture. The school's state ranking rose 16 points in three years, and that's where I learned to lead a room.

Your search can stop here.

If your team needs a manager who can steady it, grow its people and still go deep on the architecture, let's talk this week.