C-suite career advice: Sandi Lin, Skilljar
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C-suite career advice: Sandi Lin, Skilljar

 Co-ame: Sandi Lin

Company: Skilljar

Job Title: CEO and Co- Founder

Location: Seattle, WA

Sandi Lin is the CEO and Co-Founder of Skilljar, the leading customer training platform used by companies like Cisco, Verizon, and U-Haul to accelerate product adoption and deepen customer engagement. Prior to Skilljar, Lin was a Senior Manager at Amazon.com, leading product management teams for Fulfillment by Amazon, Amazon Local, and Kindle with Special Offers.


What was the most valuable piece of career advice that you received? When I first started at Amazon, a manager challenged me to always be able to get my own data. I've internalised this advice in building Skilljar, as well as in my previous roles because it enables a level of self-sufficiency and independence that would otherwise not be possible. When this advice was first given to me, I took it as an opportunity to learn skills like SQL and how to query the data warehouse. Throughout my career, these skills have enabled me to support my ideas and solutions with data without relying on analysts for support.

At Skilljar, our platform is based on data, and the ability to own and manage that data ourselves makes us incredibly self-sufficient. We've also invested in making it easy for our customers to take Skilljar data into their CRM (like Salesforce), analytics, and reporting platforms of choice.

What was the worst piece of business advice that you received? To succeed as a startup, Reid Hoffman explains you have to be both a contrarian and be right. For an entrepreneur, this means you are constantly being told why you will never succeed. In my early days, important and respected leaders and mentors told me that I would never be successful unless I was willing to run my company to the brink on cash. I was also told I would never succeed unless I moved my company to Silicon Valley and that I would never raise funds from a top-tier venture capitalist after already raising $4 million prior to our Series A round.

It's feedback like this that is short-sighted and demoralising, and it perpetuates the myth that there is only one style of startup success. Thankfully, my customers and my team were fully supportive of the business and our progress and that's where my confidence came from in those early days.

What advice would you give to someone starting their career in tech? I would encourage them to find a company and a team that will challenge you and helps you grow while providing a foundation of psychological safety.

Did you always want to work in tech? Not at all! In fact, my father and my sister have both made careers in the tech industry and I originally sought to differentiate myself from them. I majored in civil engineering in college and when I went for my MBA, I was hoping to work in clean energy or at a consumer brand upon graduation. Eventually, I realised that what I truly wanted to do was lead a fast-paced, innovative company that was changing the world around me and that the way to do that was through technology and software. That being said, I was definitely a kid who was tinkering with computers and programming as early as age 8.

What was your first job in tech? My first tech-related job was at Amazon. At that time (around 2008), Amazon was perceived as a retailer, not a technology company. But as I was working there, I could see all of the innovative things the company was doing in terms of technology behind-the-scenes and I loved the idea of using tech to change the perception of Amazon and disrupt different verticals - from e-commerce to AWS to Kindle.

What are some common misconceptions about working in tech? One of the most common misconceptions about working in tech is that you have to be an engineer or have a technical background. There are so many non-technical positions at technical companies - customer success, sales, marketing, operations - that are just as important as the technical roles. People do not need a computer science degree to work in technology and it would be great to see even more people from non-technical backgrounds getting involved. 

What tips would you give to someone aiming for a c-level position? There are four dimensions to consider when your trajectory is a c-suite position: industry, function, seniority, and company size. My recommendation, and this is based on my own experience, is to change one of these elements at a time. For example, if you come from a healthcare company where you are managing a content team, it is very unlikely that your next role will be the vice president of sales at a technology company. Even if you do get that tech job, your chances of success in that role are slim. If you surround yourself with smart, encouraging people and maintain a mindset of growth and continuous learning, every role you occupy will be meaningful. Don't try to change too many dimensions at once, stay humble and know that the process will take time. 

What are your career ambitions and have you reached them yet? I want to build a category-defining, market leader in enterprise software and as part of that, I would love to ring the bell at our NASDAQ IPO one day. I'm not there yet, but I'm thrilled with how far I've come, how Skilljar has grown, and what's coming in the future.

Do you have a good work-life balance in your current role? It's an ongoing evolution. I like to follow Randi Zuckerberg's "Pick Three" concept for entrepreneurs. The idea is to prioritise three of the following: work, sleep, family, fitness or friends. It's always been helpful for me to have that framework in mind.

What, if anything, would you change about the route your career path has taken? I've always been a continuous learner and foundationally, even though my career might look random, there are common threads of creation, analytics, and problem identification and solution. I love challenges and every job I've had has given me new challenges to learn from.

I would say that there are aspects of technology I would have thought about differently, had they been around earlier in my career. When I was entering the workforce, it was difficult to find professional networks and develop connections across industries and skills. Had social media networks existed in the early part of the century, I think that would have been a very helpful avenue for mentorship as I got started. 

Which would you recommend: A coding boot camp or a computer science degree? I believe this depends on your goals. A computer science degree will provide you with a strong foundation for an engineering career and teach you valuable problem-solving skills. On the other hand, a coding boot camp will give you the skills to write lightweight apps, but may not be sufficient for a software engineering position. That said, at Skilljar, we have an associate engineering programme that enables us to continue to work with employees who have a coding background and the potential to grow further into their skillset. My co-founder Jason Stewart likes to compare it to learning a language - you can spend four years in an intensive study programme and become fluent, or you can take a three-month intensive study and have a base-level of conversational abilities. Both paths have value, it just depends on what you are looking for as the end result. 

How important are specific certifications? Certifications are important because they show mastery of a specific set of knowledge. Particularly for an industry like IT, when the subject matter is constantly changing and needs to be regularly refreshed, certifications provide a clear signal that an individual has mastered a certain level of competency. That being said, it is important to recognise that certification does not necessarily reflect an individual's potential or aptitude.

What are the three skills or abilities you look for in prospective candidates? The first skill I look for in a prospective candidate is critical thinking - when presented with a problem, how are they able to put a framework around that problem and use data to evaluate and solve it? I also look for people with a customer-focus. This means the ability to put yourself in your customer's shoes and figure out what is meaningful to them, as opposed to what is important or convenient for the candidate themselves. Lastly, I look for people with a high level of integrity. For me, people who communicate well, are honest, straightforward and do what they say they will, are the most critical. Life happens, obstacles happen and if people are able to effectively communicate those challenges and create new plans, that is essential.

What would put you off a candidate? There are a few warning signs to me when I'm interviewing candidates, in particular, arrogance and an inability to provide specific examples for questions. No one (and no project) is perfect and I'm looking for employees who are flexible problem-solvers and who understand that forward progress is a team effort and not necessarily linear.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? The most common mistake made by candidates is not being prepared. On more than one occasion I've had candidates ask me who I am and what I do at Skilljar. Not doing even the most basic of research shows me that an interviewee is not truly invested in the job. Relatedly, it is also important for candidates to express their enthusiasm for the role and the company. I've encountered many candidates who spend the bulk of the interview talking about themselves and why they are broadly interested in the startup world. The more specific candidates can be - about their experience, their interest in the company, what they will bring to the table - the better.

Do you think it is better to have technical or business skills - or a mix of both? I certainly believe in a mix of skills and do not see the two categories as mutually exclusive. In my mind, business skills equate to soft skills like problem-solving, communication and analysis. Technical, or hard skills, refer to activities like writing code or design. With this differentiation in mind, technical skills are those you can learn in a classroom and they change over time, so it's important to have a strong foundation. Business skills are harder to develop, and they can be contextual based on the company and job, but they will be important regardless of your role or industry. It is always good to identify those soft skills that you need to work on - no one is born knowing how to communicate, much less knowing how to communicate sideways and upwards. 

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