Welcome to episode 96 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_), two Pre-Sales Technical Engineers who are hoping to bring you the IT career advice that we wish we’d been given earlier in our careers. In today’s episode we discuss sponsorship, dreams, and the path to entrepreneurship with Ashley Connell of Prowess.

Original Recording Date: 09-30-2020

Topics – Sponsorship, Dreams, and the Path to Entrepreneurship

02:20 – Meet Our Guest, Ashley Connell

• Ashley Connell is the CEO and Founder of Prowess, an organization that helps companies find expert talent by vetting and certifying talented women who took time off from the work force in some way and want to get back into it.
  • The candidates could be caretakers, a leader who wants to take a step back, or someone who is after a career pivot.
  • Prowess has built a job matching platform that matches not only skills and expertise to roles but also communication style, behavior style, personality style with the team the person would be joining. This produces a better candidate fit to the role.

3:28 – Finding Spiceworks and A Fairy Godmother

• She graduated from The University of Texas at Austin with a degree in public relations but had no intention of pursuing a career in it.
• Ashley started looking for internships in Marketing and stumbled across a small company in Austin called Spiceworks.
  • She knew nothing about technology at the time but saw they had an opening in entry-level Marketing.
  • Listen to Ashley’s story about the interview with her would-be manager and how it didn’t go exactly as she thought it might.
  • In any case, Ashley became Jen Slaski’s first Marketing hire.
  • She became a guinea pig for different Marketing projects. Once she tested them and got them off the ground they could be handed off to someone else.
  • Ashley worked in the Austin office for about 4 years and then moved to London for a couple of years and helped open an office overseas, which helped her see Marketing from a global perspective.
• John and Nick originally met through the Spiceworks community. In much the same way, Nick met Ashley when she worked for Spiceworks at some local meetups in Austin.
• Nick digs into Ashley’s interview with Jen Slaski a little deeper. She was slightly overdressed for the interview and the culture at Spiceworks.
• Ashley was comfortable with asking questions and not knowing things. When talking to IT Professionals in the community, she made her role clear (helping to amplify the Spiceworks brand and connecting Marketers to IT Professionals). It wasn’t to know everything about technology.
  • At the end of the day, Ashley’s knowledge of technology didn’t matter. People were more focused on building community than on their differences.
• 9:09 – What about the gender imbalance in the Spiceworks community and greater technology industry?
  • The hard part about being a female is you do not know someone’s intention. You want to assume the best, but when people want to take you to coffee for career advice, for example, it may or may not be what they are bringing to the table.
  • Spiceworks was a safe spot, but there were comments here and there that were inappropriate. Sometimes she had to pretend she didn’t hear them, which is horrible.
    • If she could go back and change something, she would have said something.
    • John makes the point that it is difficult early in your career to stand up to yourself in front of peers.
    • Ashley talked to some women younger than her about these situations later. She had originally thought staying in those situations / being considered one of the guys was a good thing or a way to progress her career. "You should not have to be a part of the boys club to get to the next level."
    • John says this is like a tacit allowance of harassment. It should be a constant 0 on the scale rather than getting to even a 1.
    • Spiceworks was good at spotting this and calling it out, but at places later in Ashley’s career, the organizations weren’t so good about it.
    • Even for males, why be considered one of the boys if that means allowing harassment?
    • Many women in the tech industry leave their roles because of sexual harassment.
    • For our male listeners, if you see something, say something.
• Ashley was involved in building Spiceworld, the annual Spiceworks conference which began in 2008.
  • Listen to her story of when the conference was hosted at the Alamo Draft House in Austin.
  • Putting on a conference like this makes you think through a number of backup plans for failure scenarios. When people pay for a 3-day experience, there is a lot of pressure to make things work.
  • The Spiceworks community was great at giving feedback, whether good, bad, or ugly. It came from a genuine desire to improve things.
  • There seemed to be a secret sauce behind Spiceworks and their community.
    • There was empathy among IT Professionals, with Tech Marketers, and with Spiceworks employees.

19:19 – That’s What Dreams Are Made of

• When Ashley got to move to London, it was her dream.
  • She studied abroad in college and really enjoyed it.
  • During her interview with Jen Slaski, Ashley mentioned wanting to go back to Europe as a career goal. As it turns out, Jen orchestrated a way for Ashley to reach that goal by helping to open the European Spiceworks office.
  • Ashley refers to Jen as her "real life fairy godmother."
  • Finding mentors, champions, and sponsors early in your career is incredibly key to get to the next level.
    • Sometimes we stumble upon these folks, and other times we have to seek them out diligently.
    • In every stage of your career you need coaching. John gives the example of Tiger Woods at the top of his game still needing a coach.
    • Great quote – "Managers talk to you. Mentors talk with you. Sponsors talk about you."
    • This is part of that internal marketing we all need to do so people know who we are and what we are doing to make the organization more valuable.
  • Great managers find a way to help their employees meet career goals and can help retain talent while promoting growth.

24:16 – Life at The Big Corporation

• Ashley left Spiceworks and worked for a small startup after coming back to Austin.
• She quickly realized she was doing all the same things she had done while at Spiceworks.
• A superstar is always wanting the next opportunity. A rock star wants to be steady and be an expert in one thing.
  • Each of these personas has different types of motivations. Ashley is a superstar.
• She was recruited by SanDisk next, which was her first big corporate company. It was critical to her understanding of how big companies work.
• 25:16 – The role required a great deal of travel (50% of the time she was away in the Bay Area).
  • She was able to get to know people higher up in the company, and they were able to get to know her.
  • As in the past, the line was crossed a bit in some of these activities, which caused discomfort. There were a bunch of 1s that happened at this company.
• Ashley was eventually laid off. In fact, she was offered to either interview for her current position at 30% less pay or take a severance package.
  • She chose to take the package (an easy decision).
  • This caused no emotional downturn. Being an entrepreneur at heart, Ashley was ready for her next pursuit.
  • Working for big companies with a very structured promotion plan does not work well for Ashley. It may not suit her ambition or progression goals. She realized this just was not for her.
  • This is a lesson in finding out what a growth trajectory within the company is like. John mentions knowing to ask about this in interviews.
  • When you bring in a spouse / partner, it is not just your decision in these types of situations. Sometimes there must be trade offs on who takes the career risk.

31:54 – The Entrepreneur Bug

• At this point, Ashley had the entrepreneur bug and started a Marketing consulting firm with some folks from SanDisk (A10 Partners).
  • She made so many mistakes during this experience.
  • It does not feel like failing when you’re in it.
  • The entrepreneur bug started piece by piece with her experience at Spiceworks and then SanDisk.
  • The biggest mistake at this consulting firm was having a "whale" client.
  • Ashley worked with 2 other partners with much more experience than her.
    • As a result, she hid her voice within A10 for a long time because of her perceived low rank. Ashley went along with ideas she wasn’t sure about as a result. She did not feel safe enough to expose weakness.
    • She realized much later that not taking a more active role in activities like brainstorming was a missed opportunity.
    • The culture was not one in which they could afford to have anything less than great ideas. The A10 client base was large tech companies, and these companies relied on the A10 team to be polished experts who always had the right answer.
    • John makes a great point about this having to do with career inexperience, which can affect all of us.
  • John references the TV show House, M.D. and relates it to Ashley’s predicament at A10.
    • This dove tails nicely into diversity. You need a number of different views to get the best product in the end.
    • Make sure your teams come from different backgrounds and have different experiences.
    • Ashley shares her thoughts on culture fit vs. culture add. The latter makes the team better.
    • John makes a reference to a county fair competition in which laymen guessed weight more accurately than experts. The Wisdom of Crowds
      • This is about diverse points of view
    • Nick points this back to Range by David Epstein and continues to buy into the idea of late specialization and varying experience.
    • Go back and listen to Paul Green’s description of a team very much like this. Start around 33:16.
• 46:55 – Culture in small teams
  • A10 dissolved because they lost their "whale client."
  • After this kind of thing happens, it is difficult to think about what’s next. They decided to stop operation shortly thereafter but remained friends.
  • Entering into a business partnership means having a plan for when the partnership dissolved. Don’t think about your marriage like this.

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