Job Title: Chief Strategy Officer
Location: California
Scott Castle is Chief Strategy Officer at Sisense, leading go-to-market strategy, product management and operations, accelerating the alignment and delivery of Sisense’s product-engineering organisations. He brings more than 25 years of experience in software development and product management at leading technology companies including Adobe, Periscope Data, Electric Cloud (acquired by Cloudbees), and FileNet (acquired by IBM).
What was the most valuable piece of career advice that you received? The best career advice I’ve ever been given is to always look to hire people who can do the job better than you can, and to find that talent and delegate to it. I never want to be the smartest person in the room – I look to build teams that are better than I am, and that I can help by guiding and prioritising, not dominating or micromanaging. This strategy has always paid dividends.
What was the worst piece of business advice that you received? Over my career I’ve had a few folks encourage me to find ways to develop strategic or technical leverage over my customers – artificial stickiness – so that they have no choice but to use my products. This is terrible advice – not only do customers immediately recognise this strategy, but it never holds for long and it breeds long-term resentment that is extremely hard to mitigate. My most successful products have had low switching costs, high customer satisfaction, and have been built by listening carefully to customers and non-customers alike about what problems they’re trying to solve, not what business problems *I’m* trying to solve.
What advice would you give to someone starting their career in IT/tech? Frequently ask the question “what is the user trying to accomplish, and why?” – bad requirements won’t make sense, and good requirements will be far easier to satisfy with this context. And more importantly, an understanding of the user will foster an understanding of pretty much everything else, over time.
Did you always want to work in IT/tech? Actually, I wanted to be a marine biologist – but I was fascinated by technology from an early age, started coding in earnest at ten, and was online as soon as I could lay hands on a modem. By the time I wanted a ‘career’, technology seemed like the obvious choice.
What was your first job in IT/tech? My first ‘real’ software gig was a brief high-school internship at GTE, coding some of the first CGI-BIN applications for the web back when everything was stateless and context was passed entirely in the query string. This was great because I was basically given an IIS server and a C++ compiler and no other guidance, so there was a lot of room to make mistakes and try new ideas.
What are some common misconceptions about working in IT/tech? The most pernicious one I still run into is a belief that everyone in IT, or in tech generally, is one personality type. That was never true, and it’s even less true now.
What tips would you give to someone aiming for a c-level position? First, don’t aim for a c-level position. At some point, it will be obvious to everyone – except you, probably – that you’re the right person for that particular job. Second, on your way to that moment, be really curious how everyone else does their job and try to learn as much as you can, especially about parts of the business you don’t interact with much. There’s interesting, valuable detail everywhere that you can learn from.
What are your career ambitions and have you reached them yet? I’ve really never found career ambitions particularly helpful. I get curious about how things work – technology, business models, sales teams – and I look for chances to try those things out, to learn, and to satisfy my curiosity. Wanting a specific title or role or job in and of itself is chasing a mirage.
Do you have a good work life balance in your current role? I’m fortunate that I’m passionate about the kind of work I do. I’d be spending a lot of my time doing this kind of stuff even if it wasn’t a job. I don’t really think about work/not-work. It’s all activity I’m interested in.
What, if anything, would you change about the route your career path has taken? I’ve had the opportunity to see so many amazing things – thousands of different companies, lots of different disciplines, many, many challenges – that’s been incredibly rewarding. A career is a complex system – it’s not clear to me what effect any specific change might have, or that it’s possible to aim reliably for a specific goal, so I don’t know what the purpose of changing something would be.
Which would you recommend: A coding bootcamp or a computer science degree? A degree. You can learn a skill or a language any time, but theory requires genuine scholarship, is relevant for far longer, and is massively more valuable.
How important are specific certifications? Tactically, they can be important. Strategically, not at all.
What are the three skills or abilities you look for in prospective candidates? Can you do this job better than I could? Can you explain what the point of this job is, and how it fits into the jobs everyone else is doing? Do you have empathy for others?
What would put you off a candidate? Using buzzwords and jargon to give the appearance of competence.
What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? One, being anything other than yourself, in the hopes that it’s possible to appear perfect for the role. Two, bringing up any resentments you have about your previous (or current) job in the hope that the interviewer will validate your resentments. Three, feigning knowledge about a topic. This is the triumvirate of ‘play stupid games, win stupid prizes.’ All three can be easily avoided by being present, straightforward, and yourself.
Do you think it is better to have technical or business skills – or a mix of both? It’s better to have both but it isn’t necessary to have multiple degrees or decades of experience in each domain. Virtually all leadership roles are ‘second careers’, beginning from mastery of one discipline, and growing through experience with a wide variety of other disciplines.
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