Head in the Cloud: SaaStr Annual 2019


These days, on every corner in the Bay Area you can spot software-as-a-service (SaaS) companies—B2B organizations firing up products through the cloud that impact the way we work and engage with one another.

Last week, more than 12,500 founders, entrepreneurs, senior executives, and VCs from the SaaS community gathered in downtown San Jose for the fifth iteration of SaaStr Annual 2019, the premiere SaaS conference in the Bay Area drawing in attendees from around the world. This was the first year the conference took place at the San Jose McEnery Convention Center and the outcome showed the event is growing more than ever.  

Attendees watched speakers from Dropbox, Stripe, HubSpot, Salesforce, Flexport, Glassdoor, and Zendesk speak about tips, lessons learned, and values held to scale and grow their companies. In addition to panels and solo presentations, the Convention Center buzzed with ongoing mentoring sessions and VC pitching.

While many sessions included best practices for scaling and growth, like “Scaling from $1MM to $500MM ARR: 5 Strategies to Drive Your Next Wave of Growth” with Karen Peacock, COO at Intercom, other sessions focused on the importance of diversity, inclusion, and culture. SaaStr continually emphasizes their mission to be the most representative and inclusive event in SaaS.

Caitlin Bartley, our Founder and CEO, moderated a panel on, “Crossing 100 Employees while Keeping Your Culture Intact” with panelists Melanie Tantingco, VP People Operations at Periscope Data, and Anneka Gupta, President and Head of Products and Platforms at LiveRamp. The discussion dived into the journey of their company growth and effective initiatives to maintain a healthy company culture and business.

Key takeaways from session:

  • As your company scales, so should your culture. Anneka (LiveRamp) reflected on how company core values are essential for a foundation to fall back on as you scale, and how it’s important to evolve your culture as your company scales.

  • Empower your employees to feel heard. Companies have a responsibility to not only offer employees the tools to succeed, but also to empower and encourage they build them. Melanie (Periscope Data) shared an example from an open employee forum of an employee who asked why their company didn’t have a female Employee Resource Group. Melanie’s response? “Because you haven’t started it.” Ensuring transparency and providing opportunities and resources for employees to address any issues they have are essential in keeping a healthy and inclusive culture.

  • Keep your values visible and top of mind. Periscope Data keeps their eight core values top of mind for employees, from displaying their values on screensavers to having one employee present how they’ve implemented one value at their weekly all-hands.

  • Churn is okay. Preparing for churn is important logistically, but even more so, the exit process should be a positive experience for an employee. Anneka discussed why she believes many of LiveRamp’s employees “boomeranged,” or returned to the company, after leaving. She emphasized the importance of making sure employees feel like a valued teammate and celebrating their contributions.

In another session, Nicole Alvino, Co-Founder and Chief Strategy Officer at SocialChorus, reflected on her time in structured finance at Enron and and lessons learned from working in a toxic company culture. Nicole shared key lessons on values she took from her experience and learned to implement in her future companies, such as valuing transparency, getting rid of the bad apples, and empowering your employees to have a voice to speak up.

Beyond funding, product innovation, and tactical strategies to upmarket, SaaS leaders expressed the importance of company culture, values, inclusivity and how these elements can make or break the most successful startups in SaaS.