Interview with Sandi Lin, CEO, Skilljar

Sandi Lin, CEO, Skilljar

“Companies need both great product and great go-to-market in order to succeed — It’s very difficult to keep customers happy in the long-term if the product isn’t meeting expectations.”

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Tell us about your role at Skilljar. What inspired you to establish a customer-training focused company?

I’m the CEO and Co-Founder of Skilljar. We started the company in 2013, and have grown now to roughly 75 employees in Seattle and several hundred customers worldwide. My Co-Founder (Jason Stewart) and I were captivated from the start by the idea of using technology to improve knowledge sharing and democratize learning.

We actually pivoted a few times in the early years with various product ideas in the online education space. The most recent before Skilljar was a learning platform targeted at individual instructors and authors, and luckily larger companies started finding and adopting the platform in 2015. We leaned into that momentum and partnered closely with those early customers to further develop the Skilljar product into the robust customer training platform it is today.

Tell us more about Skilljar’s technology and your target audience.

Skilljar is the leading customer training platform for companies to improve product adoption and customer retention. Unlike HR learning platforms, Skilljar was designed from the ground-up to deliver external-facing product training to customers and partners. The platform consists of a next-generation learning experience, flexible access and payment controls, robust content management and reporting tools, and enterprise-ready integrations with other customer-facing systems including Salesforce CRM.

We primarily serve mid-market and enterprise B2B companies such as Zuora, Zendesk, and Smartsheet. We also have many outstanding customers in the insurance, transportation, healthcare, customer service, and manufacturing industries.

What are the differences in the challenges faced by SMBs and Enterprise clients, in leveraging customer-training to drive ROI?

My time at Skilljar has taught me that customer training can drive tremendous ROI in every company size. However, it’s most applicable at mid-size companies (say 500 to a few thousand employees), as there has typically already been a decision at that size to invest in customer success and/or services. In addition, this segment of companies is typically interested in technology systems that scale, and prefers online training to classroom education. An additional bonus with this segment is that we are fortunate to see many of our customers going public!

Larger enterprises are usually already staffing a large customer training program, and understand the value. The challenges there may be shifting the mix from classroom to online, finding the resources to approve and integrate technology systems (e.g. Skilljar to Salesforce), and navigating internal signoffs that might be necessary for content and visual updates.

What is the hardest part of avoiding customer churn?

Companies have long invested in new customer acquisition functions such as Sales and Marketing, which have a relatively short timeframe (weeks or months) to pay off. But the journey is really only just beginning when the contract is signed, and the customer’s clock starts to count down to the renewal conversation.

Making customers successful is something that must be worked on constantly and proactively throughout the lifecycle of the contract, starting with proper onboarding and driving customer value as quickly as possible. In addition, customer outcomes are an ever-shifting combination of human factors (e.g. executive sponsorship), business drivers, and product usage. It takes much more effort to help customers achieve success in light of the uncertainty and constantly changing environments.

I find that much of the dialog around customer success and churn focuses on renewal mechanics. But that’s like avoiding a divorce with a last-minute attempt at therapy, versus working on building a healthy relationship over days, weeks, months, and years. The latter is much harder than the former, but pays off in the long run.

Tell us a little about integrating Skilljar with a CRM, especially Salesforce.

Integrating Skilljar, a customer training platform, with a CRM is absolutely critical. The CRM is usually a company’s source of truth about customers, so incorporating data about training activities into the CRM helps a company track training uptake as a leading indicator of customer health, and also quantify ROI of training on customer health and retention.

Many of our customers also sell training as a product SKU. In these cases, it’s important to drive orders and provide the appropriate training products directly from Salesforce. Otherwise, there is a lot of manual effort, wasted time, and data errors, which drive sales, training, and finance teams crazy.

How do you go about training and development to achieve customer success?

Product adoption is a key driver of customer success, and adoption comes down to awareness and usage. Awareness — is a customer aware of best practices and the various aspects of an ever-changing product? Usage — does the customer know how to utilize the product to its fullest extent? Both of these areas can be solved through customer education, both during initial implementation and then ongoing user onboarding.

According to you what is more important, building a great product or keeping your customers happy and why do you believe so?

Wow, that’s an incredibly hard question. The reality is that companies absolutely need both great product and great go-to-market in order to succeed. I think it’s very difficult to keep customers happy in the long-term if the product isn’t meeting expectations. However, product is only the first step in driving customer satisfaction, and sometimes isn’t sufficient to achieve the customer’s desired outcomes. So, I’d have to vote for great product, because it provides a solid foundation on which to build a sustainable customer base.

How important is the role of Artificial Intelligence in the customer-training domain?

The jury is out, but my sense is that AI will be less important in customer training than in other functions or industries because there is comparatively less data to process (than say, healthcare) as well as a looser tie to revenue outcomes (than say, e-commerce sites). That being said, my co-founder actually led the development of a Machine Learning-based personalization engine while at, and we recently unveiled a Skilljar course recommendations feature based on similar technology. We’ll be tracking developments in this space closely to align our future product investments.

What Sales and Marketing technology tools does Skilljar currently use?

We’ve recently invested heavily in our technology stack. We use HubSpot Marketing Automation, ZoomInfo, LinkedIn Sales Navigator, Outreach, Drift, Intercom, Zoom web conferencing, Salesforce CRM, DocuSign, and Zendesk.

What is that one standout feature in Skilljar’s technology that sets it apart from the rest?

Our Salesforce integration is hands-down the best on the market. It enables our customers to tie training activities back to account metrics such as value, retention, and health. This integration also facilitates personalized customer journeys that incorporate a holistic view of customer activities from a variety of systems.

Most learning platforms were designed for HR and employee training, so they typically don’t have a Salesforce integration or at best were designed for sales training. Skilljar was specifically built for customer training, and our Salesforce app reflects that. Finally, we are official ISV partners, including passing an extensive annual security review that Salesforce conducts on all approved apps.

As a business leader, where do you see the customer-training industry in the next five years?

According to industry studies, 80% of customer training is still performed in the classroom. In five years, I believe this will be flipped, and the majority of customer training will be online and self-paced. Not only is there a generational shift in learning preferences, but it’s also simply too expensive, inefficient, and unscalable for companies to rely on classroom training for product education. There will still be a role for in-person instruction, but it will become secondary to online learning.

What apps/software/tools can’t you live without?

From a work perspective, I’m completely reliant on Google apps (email, calendar, docs, sheets, maps), Salesforce, LinkedIn, and Lever (our applicant tracking system). From a personal perspective, I spend the most time on Instagram, Pokemon Go, and Overcast (for podcasts).

What are you currently reading?

I typically read several books a week. I just started “Never Split the Difference: Negotiating As If Your Life Depended On It,” which is written by a former FBI hostage negotiator. I recently finished “Educated” (by Tara Westover), which is an excellent memoir, as well as Bad Blood (by John Carreyrou), a story about the rise and fall of Theranos.

What is the best piece of professional advice that you have received?

The most impactful advice I’ve received was from my summer internship during junior year in college. I was an associate consultant intern at Bain, a management consulting firm, and was taught to be “zero-defect” in both analysis and presentations. Furthermore, when presenting potential next steps to a client, I was expected to have already come up with and vetted the implementation plan. This internship exposed me, at a very young age, to the level of intellectual rigor and presentation quality that is expected by Fortune 500 executives.

Who is that one person from the industry you would love to hear these answers from?

Bill Binch, CRO at Pendo.

Thank you, Sandi! That was fun and hope to see you back on MarTech Series soon.

Sandi Lin is the CEO and Co-Founder of Skilljar, the leading customer training platform used by companies like Cisco, Verizon, and Tableau to accelerate product adoption and deepen customer engagement. Prior to Skilljar, she was a Senior Manager at, leading product management teams for Fulfillment by Amazon, Amazon Local, and Kindle with Special Offers. Sandi has bachelor’s and master’s degrees in engineering from the Massachusetts Institute of Technology and an MBA from the Stanford Graduate School of Business.

Skilljar Logo

Skilljar delivers an innovative training platform which enables businesses to provide scalable and effective customer education. The enterprise-grade solution is used by hundreds of companies to accelerate customer onboarding and product adoption by enabling multimedia course creation, an intuitive and mobile-responsive learning environment, and automated CRM data integrations. Founded in 2013, Skilljar is based in Seattle and backed by top-tier venture capital firms Mayfield, Shasta Ventures, and Trilogy Equity Partners.

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The MTS Martech Interview Series is a fun Q&A style chat which we really enjoy doing with martech leaders. With inspiration from Lifehacker’s How I work interviews, the MarTech Series Interviews follows a two part format On Marketing Technology, and This Is How I Work. The format was chosen because when we decided to start an interview series with the biggest and brightest minds in martech – we wanted to get insight into two areas … one – their ideas on marketing tech and two – insights into the philosophy and methods that make these leaders tick.

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