How to build a cybersecurity startup after years as an enterprise CISO — with Ian Amit
Building a startup is an invigorating endeavor but demands courage, careful planning, strategic thinking, and adaptability. Determined effort is required, and success is never guaranteed.
So how does someone with years of enterprise-level leadership success choose to make the move to startup founder?
As Ian Amit, CEO and co-founder of Gomboc, will tell you, there are many advantages to the transition from enterprise to startup. Ian served in various leadership roles such as CSO and CISO at companies like Rapid7, Cimpress, and Amazon. He has also served on numerous information security and tech startup boards. Now, he applies his robust background at these tech giants to Gomboc, with a mission to address real infrastructure problems.
Gomboc uses AI to continuously remediate cloud infrastructure vulnerabilities, delivering tailored remediation solutions for cloud misconfigurations - rather than simply identifying them.
In this episode of Founder2Founder, Ian shares his insights on startup building, especially in three key areas: what he takes from his years in corporate culture, how he chooses to leverage his extensive professional network, and how important it is to hone those sales skills – from fundraising to selling product.
Align startup solutions with real-world problems
For Ian, transitioning from a CISO position at an enterprise company to running a lean startup was an intuitive process.
“I came into it with a very clear understanding of the problem domain,” said Ian, “as I had firsthand experience living through it for the past several years while managing security for large corporations.”
Ian emphasizes the importance of aligning solutions with real-world problems. In the information security industry, it’s too easy to get lost in highly specific, overly technical solutions that lack practical application and widespread appeal.
Ian's advice is clear – understand your market, tailor your approach, and don't sell to everyone. Recognize that what's relevant for one organization may not be for another, even if they seem similar.
Having the perspective and confidence to know that his company was founded around solving real problems was immensely helpful for Ian. However, his journey wasn't without its challenges.
Starting from scratch can mean facing discomfort, operating on a lean budget, and understanding the nuances of a dynamic market. Startup founders have to ‘do their homework’ to figure out what companies will value their solutions and what those companies’ priorities are.
To be successful, the sales cycle must be very intentional and in tune with the market.
Every dollar spent should yield a tangible return
Ian's approach to running lean startup operations centers around meticulous financial planning and risk assessment. Every dollar spent should yield a tangible return. This includes everything from the coffee in the office to marketing or sales campaigns.
In your marketing and approach, it is best to be as granular as possible about your approach and the language you use to describe a problem.
For example, instead of focusing on lofty metrics, such as ‘we have to hit $2M of ARR within the first two years,’ break down those goals into achievable milestones. Set goals around securing your first couple of customers. Then, actively learn from those first achievements to bring additional value to the next few customers, and so forth.
Adopting a technical, tactical approach to planning and daily operations can help your company reach that higher-level goal.
Know when – and how – to tap into your network
Unlike many startup founders, Ian entered the entrepreneurial arena with a rich professional network. However, he remains cautious not to leverage this network for personal gain. Ian separates his startup from personal relationships, seeking feedback from VCs and other startups without introducing conflicts of interest.
By prioritizing honest feedback over friendly endorsements, Ian ensures that Gomboc's success is built on merit. This approach might be challenging in the short term, but it ensures credibility and genuine interest from potential investors and partners in the long run.
“As I am building a new company, I want to talk to new people I don’t know and get their honest feedback,” said Ian. “My first task is to get in front of people I don’t know so they can give it to me straight. I am not willing to automatically engage with my network to try to cart sales.”
Cultivate critical pitch and sales skills for startup founders
The sales cycle and fundraising rounds are critical elements for any startup leader to master. Sales skills are not innate for everyone, and Ian admits to the drain of networking and socializing. Still, he underscores the importance of actively developing these skills and being open to feedback.
With fundraising, sharpening your ability to read between the lines is also critical. People tend to speak politely or in veiled ‘corporate speak.’ They will express enthusiasm for your idea without directly telling you ‘no.’ You rarely get a straight answer if they will be investing or not. Balancing persistence with boundaries is crucial, as well as knowing when to take 'no' as an answer while remaining assertive in your sales approach.
Creating and maintaining relationships are some of the most important throughout the sales cycle. You always want to understand who you are talking to, appreciate their perspective, and value the relationships — even with people who aren’t the decision-makers. You never know what doors a relationship can open for you later on.
Therefore, Ian advises never to say no to a first meeting because you can’t know what benefits will come from it. Whether it’s a sale, investment, valuable advice, access, or a broadened network, the power of relationship building should never be undervalued in the startup environment.
Watch the full episode with Ian Amit, and check out other episodes of Founder2Founder on the Hetz Ventures YouTube channel.
