Founder, Value Strategies

Ken Callander

A nationally recognized pricing and outside counsel management leader helping legal departments move beyond the billable hour.

Biography

Ken Callander specializes in helping corporate legal departments optimize their outside counsel relationships, ensuring greater value, efficiency, and budget predictability. As part of the Advisory Team at UpLevel Ops, he partners with legal teams to implement strategic outside counsel management programs, including transitioning from hourly billing to value-based fee arrangements. His clients span industries such as technology, healthcare, construction, the sharing economy, private equity, and multinational conglomerates.

Ken spent more than two decades at Hewlett-Packard, holding leadership roles across operations, professional services marketing, international pricing, business development, and corporate marketing. He transitioned to the legal industry as Chief Marketing Officer and Director of Business Development at Davis Wright Tremaine LLP, where he led initiatives in alternative fees, matter management, new service delivery models, client feedback, and business development.

Returning to the corporate world, Ken took on the role of Head of Legal Operations and Chief of Staff to the General Counsel at Uber, where he spent several years driving strategic legal initiatives. At Uber, Ken began exploring how VBP could better manage legal services and reduce spend by aligning costs with value delivered rather than hours worked.

Ken holds a BS in Physics/Physical Sciences from Stanford University and is a Certified Pricing Professional (CPP). He is based in San Francisco.

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Recent Thought Leadership from Ken

Article | Above the Law | June 2026

Why You Should Choose Legal Ops Tools You Can Build On (Part 2)

Ken Callander on the implementation process layer that follows tool selection: workflow definition, system access, encoded business rules, audit traceability, and design ownership that determine whether agents produce defensible Legal Operations work.

Ken Callander

AI 2026
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Article | Above the Law | June 2026

Why You Should Choose Legal Ops Tools You Can Build On (Part 1)

Ken Callander on why Legal Operations buyers should evaluate legal tech for buildability and agent-ready APIs—not embedded AI demos—and choose platforms that let teams build the agents they actually need.

Ken Callander

AI 2026
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Article | Legaltech Hub | June 2026

The 20% Problem: Why Outside Counsel Budgets Keep Breaking, and Why More Discipline Will Not Fix It

Ken Callander on why 80% of matters go over budget, why hourly pricing keeps producing broken matter budgets, and why legal departments are using 2026 to move practice areas off the billable hour one RFP at a time.

Ken Callander

Legal Spend 2026
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