A Career in Technical Sales with Caitlyn Bryan Part 1/2

Welcome to episode 111 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 Technical Sales career progression with Caitlyn Bryan.

Original Recording Date: 02-08-2021

Topics – Breaking In, Progressing to the Field, and Reflecting on Women in Tech

03:35 – Getting into the Tech Industry

  • Caitlyn Bryan is an Enterprise Client Executive at VMware based in Dallas.
  • In college, Caitlyn struggled to understand technology and wanted to take a course. She ended up pursuing a track that included coding and SAP software, which she found fascinating.
    • But, she enjoyed the social aspect most of all.
  • With a Marketing major and minor in Computer Information Systems, she wasn’t sure where to go next.
    • Her sister’s friend worked for a vendor and shared an opportunity with a vendor in a Sales role. Caitlyn really enjoyed it and didn’t previously realize this industry existed.
  • Just a few years later she started at VMware (where she has been for 6 years now). She enjoys the travel aspect of her role and getting to meet different people.
  • Caitlyn stumbled into the tech industry and is always interested in hearing how others found their way into it as well.
  • There may not be a typical path to become a Technology Sales Professional that is field facing.
    • Caitlyn spent the first few years working on the inside (customer contact made via phone) learning the role. Inside sales allows you to gain some much needed experience, supports career growth out to the field, and allows you to benefit from working in an office (pre-COVID, at least) environment that supports collaboration with like-minded peers.
    • Being a part of the inside Sales team allowed Caitlyn to gain additional insight into the culture at VMware. There were birthday celebrations, quarter kickoffs, visits from executives and Marketing, etc.
    • There are operational learning advantages to starting on the inside. Imagine being able to lean over to someone more experienced in the next cube and ask for help, feedback, or insight.
    • Caitlyn had the chance to be a coach for newly hired inside Sales personnel and was energized by the talent coming into the company.

11:25 – Progressing to Field Sales

  • What makes someone want to progress from an inside role to a field facing role?
    • Some people may not have field aspirations or really enjoy the inside role.
    • Caitlyn was passionate about deals and taking the lead role. She liked the personal aspect of sitting with customers in person and building camaraderie with them.
    • There is a compensation difference in moving to the field versus the inside.
    • Field roles are usually specific to a geographic region and may require you to relocate. Some people may prefer to stay on the inside and not have to relocate.
    • John gives an illustration of how challenging getting a field role in a specific area can be. In Austin, for example, there are many tech companies with a presence in the area and thus creates some natural competition among internal employees looking to progress and anyone outside the company looking to move into a field role.
    • Caitlyn mentioned it is very difficult to make the jump from inside to the field. It’s likely easier to transfer inside the same company.
    • Caitlyn was able to gain some experience making field visits while still working on the inside. This was helpful to her resume for consideration when she did move to the field.
      • One of her former managers created a formal progression program to help personnel progress from inside to field.
      • Before VMware Caitlyn was looking for a culture of building up talent. These are the types of programs to consider when you’re evaluating a new company.
      • No one really leaves tech unless they want a drastic change. There is so much knowledge and not a lot of brand new talent coming into the field. We need to progress our people but at the same time bring in new blood.
      • Nurturing opportunities is very important (getting mentors and network building).
      • John gives the example of Oracle’s system and it being very much like a master / apprentice (i.e. learning by doing and by seeing someone model it for you).
      • Listen as Caitlyn shares an example of letting new employees ride along with her in Dallas / Fort Worth (part of VMware’s Academy program for Salespeople, Solution Engineers, and others). This is a great opportunity for the new person to learn and for the seasoned employee to learn too.

26:11 – Reflecting on Women in Technology

  • Women in technology are extremely underrepresented.
  • Some benefits are:
    • It’s easy to find a female mentor.
    • There are no lines to wait for the bathroom at technology conferences.
  • Getting more girls interested in STEM could help, but many people don’t even know the opportunities exist.
    • Be willing to coach up our children and community to create awareness.
  • You feel like you need to have a tough exterior in order to become the alpha and not seem like you are leading from an emotional / irrational state.
    • Most people in Caitlyn’s experience have been wonderful to work with, but there are some who might think you are there to deliver the coffee.
    • Listen to Caitlyn’s story from early in her career about getting asked to go pick up coffee. "I’m not there to be the waitress."
      • It’s a strange delineation when you’re one of the few / the only female in the room.
    • Listen to Nick’s story about someone shadowing him who volunteered to go get lunch.
    • As a woman, you want to take care of people and make them comfortable. You think about things like timing for lunch, for example.
      • Caitlyn had to draw an extreme line in the sand on this.
    • Listen to John’s story about a similar uncomfortable situation.
    • In Caitlyn’s story about the coffee, a senior leader from the customer made one of his employees go and get coffee, mentioning Caitlyn was the host only.
    • In Sales, you want to take care of your customers. You’re probably an extrovert. Being a woman and wanting to continuously provide value means you don’t want to be put in a weird role.
      • John mentions the host of an event does not deliver drinks to people (i.e. not a service person).
  • What about other issues for women in technology?
    • There is always a need for more female speakers. If you don’t see someone like you in sessions at conferences, you may not believe you can follow a similar path.
    • Caitlyn gave an example of a weeklong internal conference in which not a single woman was a presenter. She called it out to her leadership as a major gap.
      • This stood out to her so clearly and was mind blowing that this could happen in the last 10 years. The next conference she attended, there were more female representatives.
      • Speaking out for diversity is critical. We have some work to do.
      • John mentions a good way to judge an organization is their response to feedback. It’s more difficult to take a step back and consider a blind spot. No one wants to call their baby ugly, but we need to be vocal about how we fix these things.
    • Right now Caitlyn has another female on her team after being the only one.
      • Women can help support and find qualified candidates by evangelizing and spreading the word about the tech industry.

Contact us if you need help on the journey.

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