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Legal Career Stories: Amber Hilliard on Building a Career with Flexibility
February 10, 2026
February 10, 2026
Who chooses to work on a contract engagement basis? What kinds of opportunities exist? And what do the career paths of attorneys doing this work really look like?
We often hear these questions from attorneys at all stages of their careers. The answers are more nuanced—and often more compelling—than people expect.
In our experience, for many attorneys who work flexibly, engagement work became one of several tools they used over time to adapt to change, deepen expertise, and stay engaged in sophisticated legal work as their lives and priorities evolved.
That theme came through clearly in a recent episode of the Leveraging Latitude podcast, featuring a conversation among Latitude leaders Candice Reed, Cynthia Cutler Moon, and Amber Hilliard. While the discussion explored a range of perspectives, Amber’s career story—spanning Big Law, senior in-house leadership, and contract-based roles—offered a particularly clear illustration of how flexibility can support both professional momentum and personal goals.
Today, Amber is the leader and founding Partner of Latitude’s Washington, D.C., office, where she works closely with legal departments and law firms to provide flexible staffing solutions during periods of growth, transition, and complexity. Like all of Latitude’s partners, she is a former practicing attorney who brings firsthand experience from the roles she now helps clients and attorneys navigate.
Before joining Latitude, Amber built a distinguished career as a corporate governance, securities, and M&A attorney. She began her practice at Skadden, where she spent eight years advising public companies on complex transactions and governance matters. She later moved in-house, holding senior legal roles at several publicly traded companies, including serving as Vice President of Law, Securities & Corporate Governance at Tupperware Brands Corporation and e.l.f. Beauty, Inc.
Along the way, Amber’s work increasingly involved guiding companies through periods of significant change—M&A transactions, financial distress, regulatory challenges, and post-transaction integration. Some were direct-hire leadership positions; others were contract-based engagements that required immediate impact and a steady hand during transition.
That mix wasn’t accidental—and it became an important part of her broader career story.
Amber’s first experience with contract work was driven by a desire to strengthen and refine her professional skills.
“Initially, I went into contract work because I had an opportunity to delve deeper into securities law,” she shared on the podcast. “It allowed me to continue sharpening my skills after leaving an in-house role.”
Those engagements gave her the space to focus intensely on a specific area of practice, strengthen her expertise, and position herself as a more well-rounded corporate attorney. Rather than slowing her trajectory, the work expanded her toolkit and increased her long-term marketability.
It’s an important reminder that flexible engagements can be a strategic way to gain depth, broaden experience, and stay close to complex legal issues.
As Amber’s personal responsibilities grew, so did the value of flexibility in her career. She describes being part of the “sandwich generation,” balancing young children and aging parents, while still wanting to remain fully engaged in challenging, high-level legal work.
“I had a strong desire to continue working on really sophisticated issues that were consistent with the work that I had previously done,” she said, “and to continue my same career trajectory.”
Contract engagements offered a way to do exactly that. Amber was able to step into complex matters, provide meaningful support to legal teams in transition, and still have greater control over her schedule.
Her experience reflects a broader shift in how legal departments think about staffing. As workloads fluctuate and teams remain lean, organizations increasingly rely on experienced attorneys who can “parachute in,” get up to speed quickly, and deliver immediate value—without committing to permanent headcount before the need is fully defined.
When Amber reflects on her contract engagement work, the roles she describes as most rewarding were the ones that allowed her to step in quickly and make a meaningful impact.
“A few of my engagement roles were interim VP roles at publicly traded companies,” she shared.
Those opportunities typically arose during periods of transition—such as M&A activity, financial distress, or post-transaction integration—when companies needed experienced leadership but weren’t in a position to make a permanent hire right away. For Amber, those moments created space to do work she found fulfilling: leading teams through uncertainty, mentoring junior attorneys, and helping legal departments regain stability and direction.
The experience reinforced something she’s seen consistently throughout her career—that the ability to get up to speed quickly, provide steady leadership, and adapt to change is deeply valuable. Those same skills continue to inform her work today as she partners with attorneys and legal teams navigating similarly complex moments.
Choosing this kind of flexibility wasn’t without hesitation. Amber is candid about the internal reckoning that came with stepping off a more traditional track.
“I had to grieve my predetermined prescribed path,” she said. “I had to be willing to give that up to take on the challenge of doing something new.”
That process involved navigating assumptions—both her own and others’—about what success should look like. But once she focused less on expectations and more on what would support her long-term goals, the possibilities expanded.
“Once you take that first step and you try something, you realize you’ve developed this incredible skill set that makes you that much more marketable,” Amber explained. “You’re able to parachute into companies in the middle of major transitions, make a high impact, and pick up skills, industries, and experiences along the way.”
Those possibilities included new industries, new leadership experiences, and a career that could evolve alongside her life rather than compete with it—one that continued to build momentum rather than pause it.
Amber’s path won’t look exactly like anyone else’s. But her story offers a clear picture of what contract engagements can make possible:
In a profession that has traditionally defined success along well-established paths, Amber’s story offers a different perspective: one where flexibility is part of a long, accomplished career—used thoughtfully, at the right moments, to sustain both professional excellence and personal priorities.
For attorneys who are curious but cautious, her experience is a reminder that you don’t have to have everything mapped out in advance. Sometimes, the most forward-looking career decisions are the ones that leave room to adapt.
If you’re exploring what flexibility could look like in your own legal career, you can browse Latitude’s current contract engagement opportunities to see the types of roles attorneys are stepping into today.
Whether you're an attorney or legal ops executive looking for legal talent to assist your team or you’re a legal professional looking for a substantive yet flexible role, let us find a solution to meet your needs.