Jessica Gilmartin AMA: Best PLG Hacks with Calendly

Jessica started her career in investment banking, ran her own specialty food business, Fraiche, and has held executive roles at Asana, Honor, Lighthouse AI, and Piazza. In this AMA, we got to chat all things PLG. Calendly is seen as one of the pioneers of PLG as it was bootstrapped for its first 7 years before raising $350M.

Learnings from Running Fraiche, a specialty food business

  • Building in an industry you have no background in can be a huge advantage. In building Fraiche, Jessica went against a lot of norms that food experts said they had to follow. For example, they built their own yogurt plant and focused most on yogurt instead of a wider assortment of offerings. This allowed them to build a really unique and differentiated product with a clear target persona. 
  • Having a clear persona in mind informed a unique marketing strategy. Before their grand opening, they got a lot of great 5 star yelp reviews from “neighborhood influencers” - the hair stylist next door, waiters and waitresses and nearby restaurants. The local news publications came to them wanting to cover them
  • B2B is much harder because it’s unlikely that you have just one persona, but the learnings still apply - build your marketing strategy around the few personas that move the needle.

The 80/20 Rule of PLG Funnels

  • PLG offers a broader top funnel, but what matters is the industries and personas that comprise 80% of your monetizable base
  • Don’t double down without data.When you’re building a marketing strategy, start with more generic targeting to prioritize gaining volume and insights. Once you see what messaging is resonating with the right audiences, you can double down your spend on advertising platforms.
  • Despite much of the industry moving toward eliminating as much friction as possible upon signup, Calendly stands by more detailed forms to better qualify users 
  • Top of funnel signups are a vanity metric. Calendly used to get a crazy amount of signups because people thought they had to sign up in order to join a Calendly meeting sent by someone else, but a lot of these would be low intent. Since then they’ve completely overhauled the UI for more optimal customer education and higher-quality signups.

Marrying PLG with Sales-Led Growth (SLG)

  • Organizations that have both PLG and SLG often struggle with the two competing with each other for leads. Instead, we should view them as both essential to the customer journey.
  • A team with a strong PLG and SLG motion has expertise that spans enterprise marketing, website funnel optimization, and email nurturing. Effective collaboration across these specialties allow you to meet the customer where they’re at.
  • Data visibility is key. In enterprise you have a clean Salesforce database where you understand exactly who the decision maker is at a large account. In PLG it’s much more fragmented - 200 different people at Amazon could be using Calendly, but you may have no idea how they all relate to each other.  A good tool like 6sense helps you understand patterns by user group and align on who to nurture.

The Role of Project Management and Solutions Marketing

  • Project Management: Good project managers ensure smooth campaign launches by mitigating risks and managing resources, timelines, and stakeholders. The perfect hire is someone who loves process and procedure but also deeply customer centric - they won’t just dogmatically follow all the rules and procedures but are intellectually curious about how to make things better.
  • Solutions Marketing: This function allows for persona-based onboarding. For example, they create tailored webinars and product onboarding flows for specific functions like sales and recruiting or verticals like financial services. This ensures that the right persona gets a more personalized first touchpoint with your team.

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