#232 Aiming to be Obsolete As A Solo Principle Sales Engineer

#232 Aiming to be Obsolete As A Solo Principle Sales Engineer

Notes:

Cybersecurity is among the fastest-growing segments of our economy. With the increase in demand, there is a need for more professionals. But is it true that the cybersecurity market is difficult to penetrate if you’re a sales engineer from a completely different industry? My guest today, Damian Tommasino breaks it all down for us in this episode by sharing his own experience working as a principal SE and leading a startup in the cybersecurity space.

Damian is a Principal Security Engineer at Feroot and the Founder and Head Sales Engineer at Cyber Informants, a small startup focused on pre-sales in cybersecurity. With over a decade of experience in cybersecurity sales, Damian is dedicated to shaping the future of the field.

Key Takeaways:

  • What is a principal sales engineer and what does he do
  • Damian’s experience of being on boarded virtually and how he managed to build relationships despite the virtual setup
  • The first thing Damian thought about when he had to also create an onboarding process for SEs
  • What it was like to be the first technical hire in the company he worked with the sales leader to put together a POC, structured demo, etc.
  • One of the principal SE’s roles is to work more closely with the product manager and help fill the gaps in product management and become a direct bridge between product and development
  • Is there pressure from the founder of the company for the salesperson and SE to work exactly the way that they work?
  • Damian’s way of handling pushback from the higherups when he had to change things in the process
  • The challenges Damian faced as the first SE at a startup were exciting to solve
  • Is it true that it’s easier for a founder to sell than for a sales team to sell?
  • What challenges gave Damian a hard time solving as the first SE at a startup
  • How Damian balances being a principal SE at Feroot by day, leading Cyber Informants by night, and also being a dad to his children
  • What is Cyber Informants and how does it help the presales community?
  • The reason Damian wrote a book for SEs wanting to enter into cybersecurity on top of already building a community for cybersecurity professionals.
  • The three-pronged approach he’s attempting to do for the cybersecurity sales engineers’ space
  • Damian breaks down the differences between SaaS SEs versus cybersecurity SEs
  • His advice for anyone wanting to become a cybersecurity SE
  • Why SEs that are being interviewed are still asked to code or integrate into different platforms 
  • How to figure out if an SE’s got potential if they’re only being interviewed once or twice
  • Damian’s thoughts around certifications and does he recommend doing certifications for those wanting to break into the cybersecurity industry

Quotes:

“Any role that I’ve taken as an SE in the last decade, I always approach it looking at a way to automate my role to the point where I’m making myself obsolete.” – Damian Tommasino

 “If you use that mindset going into it, anytime you do things like onboarding, or training or learning a net new product from an acquisition if you’re taking really good notes, building bite-sized learning for those that come after you, you start to develop this pattern where it doesn’t matter if you move on to another role, another company or you grow a team. There’s always something left because you’re leaving behind this little legacy of the different pieces that got put in place to help those that come after you.”  – Damian Tommasino

“It’s not the sales process that is important, it’s the story. What story did they tell to those first customers? What was the key use case scenario that then you can reference that came out of that? And then how do you work that into your own unique dynamic as a sales team, instead of an executive team? – Damian Tommasino

“Startup life is a very different beast than working for a large organization. I think just trying to be heavy handed with it causes a lot of friction. I think that’s the part that you really need to watch for. I don’t think there’s so much about pushback, but it’s more about how you phrase it.”  – Damian Tommasino

“People buy very differently these days. There’s information everywhere, you have access to a lot of different sets of ears and communities and what we call dark social these days. That type of information in a buyer’s hands changes the way they’re not really going to buy and having a rigid playbook in a large complex deal cycle doesn’t always work with cyber. And this is why there’s a differentiation between playbooks and frameworks.”  – Damian Tommasino

“I am not a really big believer in the like hustle and grind culture. There has to be balanced. Family, first and foremost, right? I do not feel guilty when we take a vacation or there’s downtime or spend time with the kids. A lot of people would be like, well, I could be working on this, or I should be working on that. I don’t get that kind of pressure. I know when I should be doing my job, when I should be focused on Cyber Informants, and when I should be focused on my kids.”  – Damian Tommasino

“Cybersecurity has insane layers of complexity surrounding it. And that could be everything from going back to your contractual language, it could be the length of a POC, could be the length of the sales cycle. there’s definitely just a layer of complexity in the cyber that you don’t find almost anywhere else.”  – Damian Tommasino

“By all means, investing in yourself and having a growth mindset is something that’s really important to be successful in your career for the long term because the minute you get comfortable, you’ll become stagnant.”  – Damian Tommasino

“It’s not really about coming up with content. It’s just being able to talk to customers, talk to peers in that space, and have the community say these are real challenges that we deal with day in and day out. And it’s just about how do you take that and amplify it, so you can help more people.”  – Damian Tommasino

Links from the show:

Music on the show: Watchmaker’s Daughter by Reeder