Most people take job postings at face value. You either fit the requirements and apply for the job as listed by the company, or you don’t and apply to something else.

Matt sees them a little differently.

This week on our podcast, Gentle Power (Youtube | Spotify | Apple), we spoke with our friend Matt LeBaron, cofounder and CEO of Pocketbook. Matt helps large companies evaluate their software vendors, renegotiate contracts, and make smarter decisions about their tech stack. He also works as a part-time consultant with Adobe’s software procurement team.

Matt’s path into this work began at Wharton Business School, where he completed a dual MBA and Computer Science master’s degree, followed by several years working with Fortune 100 companies on their tech vendor strategy and pricing structures. He now leads Pocketbook and also works with Adobe’s software procurement team as a part-time consultant.

We covered a lot of ground on Matt’s approach to negotiations, but one part of our conversation has been living rent-free in our heads: the story of how he started working with Adobe in the first place. It began with applying for Adobe’s full-time role posting, and after some creative negotiations, Matt had crafted the role into part-time client work as part of his business.

This story is a great example of how much flexibility exists behind the scenes of a job listing, even when the opportunity looks fixed externally.

Whether you’re a freelancer, you have your own business, or you're a job seeker who’s having trouble finding that perfect role to apply to, you’ll find a ton of gold in this conversation with Matt. Listen to the full episode here.

​

Final negotiation Q&A of 2025!

Due to popular demand, we’re hosting one last live Q&A for the year on Tuesday, December 9th at 12pm PT. With the job market still posing plenty of challenges, we’ll talk through what we’re seeing and answer any specific questions you’re navigating in your own search. RSVP here.

​

How Matt turned a full-time job posting into consulting work

Matt came across a role that Adobe had listed on their software procurement team. It was intended to be a traditional full-time position, and most people would have approached it the typical way: either submitting an application as a candidate or moving on.

Matt did apply, although with a slightly different lens. He’d already spent years negotiating major software contracts for Fortune 100 companies and helping them think through vendor strategy, which was the basis for him founding his company, Pocketbook. So during the initial interviews, Matt introduced himself as someone who could do the job, and also added that he ran a small firm specializing in this exact kind of work.

He didn’t try to convince them to convert the role into a contractor position. He simply let the hiring manager know that part-time or project-based support could also be an option if that ever felt easier for the team. This small addition created the opening.

The hiring manager explained that this particular role truly needed a full-time employee, but in a different area of the team, there was a need for part-time support. That ultimately became Matt’s current engagement with Adobe, where he now works alongside their procurement team in a way that serves their needs while fitting the structure of his business.

Nothing in the original job posting hinted that this was possible. The opportunity only emerged because Matt created room for another version of the relationship.

How you can borrow this approach

If you’re a freelancer or business owner working for yourself, job postings can feel irrelevant because the opportunity feels pre-defined and exactly as-stated. Matt’s experience demonstrates that a job description often just reflects a default option, not the only option.

Instead of treating a posting that's not the perfect fit as a closed door, you can try the following:

1. Show that you genuinely understand the role as it’s written.

This matters because it signals respect for the team’s priorities.

2. Once that’s clear, offer a gentle alternative.

For example:

“I’ve been doing this type of work with similar companies, and the role aligns closely with my experience. If it ever becomes easier for your team to use part-time or project-based support, I’d be glad to talk about that arrangement as well.”

3. Give the team space to respond.

Sometimes the posted structure truly cannot change. Other times, the team is more flexible than it looks, or your note reminds them of a parallel need that was not fully defined.

People tend to assume that job descriptions, contract structures, or pricing models are fixed. In reality, many of these “rules” are simply starting points shaped by precedent or industry norms. The goal is to recognize that the underlying need is often more adaptable than what’s formally published or publicly signaled.

Matt’s story aligns with the philosophy we instill in our clients: that negotiations isn’t necessarily a give-and-take, an offer versus counter offer, a zero-sum game. Instead, negotiations can be a creative problem-solving process that all parties collaborate on to find a win-win solution.

Listen to the full conversation here: Youtube | Spotify | Apple​

Learn more about Matt and Pocketbook here: Website | Matt’s LinkedIn | Email: matt@pocketbk.com​

​

Best,

Gerta & Alex
​Co-founders, YourNegotiations.com

​

P.S. Are you job searching or have upcoming negotiations?

Book a free call with us, where we’ll learn more about your situation, offer some free tips, and explore if we’re a good fit to work together: https://calendly.com/alexhapki/call​

P.P.S. Know someone who could use our help?

Refer them and earn $500.

We’ve paid out thousands to people who just made a simple intro. If your friend becomes a client, we’ll send you $500 - no strings attached; just our way of saying thank you for spreading the word.

Simply send an intro email to alex@yournegotiations.com and your friend.

See all the details of our referral program on our website here.