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Reflections: How to Win as a Woman Entrepreneur

August 13, 2026

By Jamie Crump

When I began my procurement career, I was 19, working for a welding supply company.  I was not a procurement savant. The company I was at had several key people leave, and I was left still standing. I learned what I needed to do, and the rest, as they say, is history. 

For a long time, I was the youngest person in the room and usually the only female. I’ve avoided clumsy passes, dealt with a restroom that was full of Penthouse and Hustler magazines, been spoken to like I was a cocker spaniel, and offered everything from a new car to a mistress apartment and an expense account to guarantee the win of a contract. 

Yes, we have made a lot of progress, but consider where we started from. While I concentrated on the above, what were my male counterparts doing? Now that I am stepping back from consulting to write and tend to my health, I’ve been thinking about what epiphanies I’ve had along the way that other women might benefit from. Here is what I came up with.

1. I am almost never the person in the room who knows the least

I still distinctly remember having this revelation in a meeting including about a dozen executives. They were making it up as they went along too! The message for me was that I needed to speak up much more rather than waiting for someone else to solve the problem du jour. 

2. Life is a lot more interesting when I am the one in the room who knows the least

I want to be where I can learn. Seriously, what are the people in the first room going to teach me? Don’t just hang out with the best fountain of intelligence; hire them!

3. Know your worth

I interviewed for two of the best jobs I’ve ever had because I wanted interview experience (yes, it’s a skill set that shouldn’t be ignored). If you don’t keep up with pay in your market, you don’t know what you should be getting. Don’t wait until you need a job to look for a job. My resume was up to date from the 90’s onward. Oh, and when you open your own business, do the same exercise: know what your competition is charging. 

4. Have some fun

I enjoy my work, and so I spend a lot of my time doing it. If I’m not having fun, I am just torturing myself. I’ll try to fix it, or I’ll consider the situation. If I can fix it, I will. If not, I move on. You didn’t get the last job out there. Go somewhere you are appreciated, trained better, working with fewer jerks, or all of the above. 

5. You don’t always get to choose who you work with

Nothing will be fun 100% of the time. You must decide what your parameters are. I can be quite successful with someone I would never have cocktails with over the holidays. They don’t have to like me either as long as it isn’t disrespectful or against my ethics. 

6. The most precious thing you have is your network

I’m not talking about how many connections or followers you have on LinkedIn or Instagram. I’m talking about someone who will take your call when you need them. Guess how you get them to take your call? You take theirs when they need you. There are people in my network that I talk to once a year, and we pick right up where we left off; others that I check in with once a month/quarter, etc. The point is, take an interest. Isn’t it nice when people do that for you? 

7. Intelligence comes in all forms

I worked with someone who had three PhD’s. They couldn’t change the toilet paper roll in the bathroom. But you know, that’s not what I hired them for. They turned out patentable inventions faster than anyone I’ve ever met or read about. Everyone brings something to the table. Don’t expect it to be just like yours (and wouldn’t that be boring anyway). 

8. It is almost never about you

Nothing is more boring or a greater time waster than office politics. My observation is you can waste a lot of time listening to someone who never, ever gets any piece of information first. Even worse, they will spend endless hours speculating on what their boss, co-worker, department contact, customer, supplier - thinks or says about them. The truth is that all of those people don’t spend five minutes thinking/talking about you, so get some work done or pick up a hobby. 

9. Find your balance

No one on their deathbed ever said they wished they had taken another meeting. Your happiest place should not be your office. If it is, get busy because you have a lot of work to do. Family, loved ones, hobbies, rest, exercise, relaxation, and the general detox from everyday life are more important than the job. If you aren’t getting it, it will take a toll. 

10. Stay curious

Had I been born rich, I would have spent my life traveling and attending classes at universities and workshops around the globe. Alas, it didn’t turn out that way. So, I read an hour a day (usually more on weekends) and I read 60 books last year. I usually take a couple of workshops or certificate programs each year. If you end up sitting next to me at an event, I will know more about you than anyone else at the table. You do you, but keep casting a wider net. One conference rule I have is to not sit at a table where I know everyone. If you’re not curious, you are stale. 

There are many more, but I believe it covers most of what’s important. I hope one or two help you and I would love to hear what yours are. I’m curious, after all.  I welcome our conversations; please email me at  jamiescrump@gmail.com 

About Jamie Crump

For 25+ years, Jamie has focused her career in strategic sourcing and supplier diversity across a variety of industries including banking, catastrophic insurance, heavy equipment rental, IT, pharmaceuticals, telecommunications, welding, and medical supply.

Until recently, Jamie served as WBE Canada's Lead Consultant, where her expertise, leadership, and passion helped advance our mission and strengthen our impact. As she turns her focus to her health and her writing pursuits, we look forward to her continued voice and advocacy in championing supplier diversity, inclusive sourcing, ESG, and the success of women-owned businesses. Her insights and commitment will continue to inspire organizations and entrepreneurs alike as they navigate today's evolving and often challenging economic landscape.

Jamie Crump is the author of Backstage Pass: Pulling the Curtain Back on the Business of Supplier Diversity that looks at how a supplier diversity strategy intersects with other areas of the business.  She is a frequent global speaker on procurement, diversity, and leadership topics. Her latest white paper is entitled Rumors of My Death Have Been Greatly Exaggerated: How Supplier Diversity Will Thrive in 2024 and Beyond