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Bill Caldwell

@billcaldwellsr

Solutions Engineer | Customer-Facing Technical Leader | Enterprise IT, Govtech & SaaS | Former buyer-side, now vendor-side

United States

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What I'm looking for

I’m looking for Solutions Engineer, Sales Engineer, Customer Success / Technical Account roles, or senior IT leadership opportunities in the Bay Area or remote, where I can solve hard technical problems and help customers adopt the solution.

I live by Edison's line: success is going from failure to failure without losing enthusiasm. When a problem matters, I'll find 10,000 ways that don't work before I quit. But I do that failing behind the scenes. By the time I'm in front of your customers, I'm bringing the solution that works, not the experiment. Nobody wants to be the guinea pig.

That's the whole job: figure out the hard technical thing in the lab, then get real people to actually adopt it in the wild. I'm the person you bring in when the project is a mess, the last three attempts failed, and the users are convinced it'll never work. That's my favorite kind of problem.

Over 20+ years I've gone from network labs and restaurant operations to enterprise IT engineering and running an entire IT department. The through-line: solve the hard technical thing, then get people to embrace it. A rollout isn't done when the tech works. It's done when the customers are happy and it sticks.

I give people the honest read paired with a way through it. The real situation, the real odds, and a surmountable path forward, even when that path is a pivot they didn't expect. Customers remember that and keep you on speed-dial for it.

Some things I'm proud of: an enterprise cloud migration at Alameda County (20+ departments, 8,000 users, 30TB) that won over departments that had fought every prior attempt. Rolling out a Digital Evidence Management System and a portfolio of AI-enabled vendors into a DA's office that had said 'no' to new tech for 20 years, driving six figures in annual savings. Leading a ~30-agency effort (eSCARS) to replace fax-and-mail child-abuse reporting with a near-real-time system. Earlier, in sales engineering, hitting President's Club at nearly 200% of quota.

Open to Solutions Engineer, Sales Engineer, and Customer Success / Technical Account roles, plus senior IT leadership. Bay Area or remote.

Experience

Work history, roles, and key accomplishments

Director of Information Technology

Alameda County District Attorney's Office

Dec 2022 - Feb 2026 (3 years 2 months)

Ran IT for a 400+ person District Attorney's office across 13+ locations with a 5-person team and 40+ applications: enterprise project delivery, vendor strategy, CJIS compliance, and top-tier executive support. Inherited a department that had resisted technology change for two decades and turned it into one that started requesting new tools.

• Drove six figures in annual savings across the vendo

Infrastructure Services Analyst

Alameda County Information Technology Department

Jul 2019 - Dec 2022 (3 years 5 months)

Customer-facing infrastructure analyst in a high-standards county IT department, owning enterprise rollouts end to end: the engineering, the project management, and the change management that actually makes adoption happen. Known as the person who could systematize a rollout others had given up on.

• Spearheaded an enterprise OneDrive/SharePoint migration (20+ departments, 8,000 users, 10,000 en

Information Technology Instructor, Externship Coordinator, Content Advisor

Unitek College

Oct 2017 - Jul 2019 (1 year 9 months)

• Taught eight accelerated IT courses (CompTIA A+, Network+, Security+, Cloud+, MCSA Windows 10, Windows Server 2012 & 2016, MS Office) while simultaneously rebuilding a failing externship program from the partner, student, and process sides at once.

• Personally kept the Fremont externship program from being shut down, lifting placement-to-hire from roughly 25-33% (below the 50% accreditation m

Operations Manager

CREAM, Inc.

Jun 2013 - Nov 2015 (2 years 5 months)

Hired to bring structure to a fast-growing dessert and catering brand, running planning and day-to-day operations across multiple franchise locations: inventory, quality, marketing, and a 50+ person staff.

• Built Standard Operating Procedures and Excel-based cost and scheduling models that cut labor costs ~20% and lifted profitability, while keeping customer satisfaction high. (Even in the rest

General Manager

Round Table Pizza

Oct 2008 - Jun 2013 (4 years 8 months)

• Ran a profitable $1.4M franchise in a fiercely competitive market, owning P&L, staff, marketing, and operations.

• Grew profitability ~3% year-over-year across a five-year period.

• Launched marketing programs (using design software and a lot of creative energy) that drove steadily increasing customer counts.

• Earned consistently high marks from the head office and trained the next genera

Senior System Engineer

Spirent Communications

Oct 1999 - Sep 2004 (4 years 11 months)

Spent five years across systems engineering and sales for a leading network and wireless-communications test company, and chose to move back into a technical seat after a stint in sales management, because customer-facing technical work is where I do my best work.

• Year one: hit President's Club at nearly 200% of quota. The following year I was promoted to Regional Sales Manager and took the co

Senior Network Technician

net.com

Apr 1997 - Oct 1999 (2 years 6 months)

• Ran lab management and proactive support practices in the premier development lab for a leading network-equipment provider serving government and enterprise customers.

• Led the overall ATM lab-environment design for the Systems Test Engineering Team, including the patch-panel redesign for a major lab relocation project.

• Set a new standard for cable and equipment installation: professional