Introduction: The Glean Journey
AJ Tenant, VP of Sales and Customer Success at Glean, and Lauren Kennedy, Head of Customer Success, took the stage to share how they scaled Glean from a handful of customers to hundreds, with 100x end-user adoption and nearly a million paid seats.
AJ brought experience from Slack, where he helped grow ARR to over $1B, and Facebook (now Meta). Lauren, a Gainsight alum, brought her expertise in building customer success teams at startups. Together, they joined Glean in 2022 when the company had just dozens of customers, a few thousand users, and a few thousand paid seats.
Fast forward to today: Glean has undergone a full brand refresh, multiple product releases, and a recent funding round. But the real story is how Sales and Customer Success (CS) worked together to drive this explosive growth.
4 Unexpected Learnings:
- Community-Led Success Beats 1:1 Channels – Glean scrapped 50+ individual customer Slack channels for a single community channel where customers help each other, unlocking new use cases and scaling support.
- “Collaborative Tension” Drives Innovation – Glean’s leadership intentionally creates productive friction, challenging team members to improve rather than accepting “good enough.”
- Security Concerns Became a GTM Asset – By deeply engaging with customer security fears, Glean transformed potential objections into product features that now strengthen their sales pitch.
- Multi-Threading Is Systematically Tracked & Incentivized – Glean tracks multi-threading metrics in Salesforce and offers quarterly “spiffs” (incentives) to team members who establish the most stakeholder connections.
4 Things That Didn’t Work Well at Glean:
- Individual Slack Channels Became Unsustainable – The initial high-touch approach with dedicated Slack channels for each customer created an unscalable support burden that was “breaking for both Glean and its customers.”
- Relying on Champions Without Executive Buy-in – Glean learned the hard way that customer champions alone weren’t enough; when champions left organizations without executive relationships in place, entire accounts were at risk.
- Insufficient Prompt Guidance for Users – Early users struggled with knowing how to effectively interact with the AI system, requiring Glean to develop prompt libraries and more user guidance.
- Selling Without Case Studies Was Inefficient – The early days of category creation without customer success stories led to longer sales cycles and more resource-intensive pre-sales processes.
The Early Days: Selling a Category That Didn’t Exist
Glean was founded in 2019 by Arvin Jain, a former Google search engineer, to create the category of workplace AI. The platform indexes corporate data, builds a Knowledge Graph, and navigates complex security and permissions.
But here’s the catch: No one knew they needed it.
“We were selling a product that customers saw as a nice-to-have, not a must-have,” AJ explained. “Our challenge was to change that perception.”
Key Tactics in the Early Days:
- High-Touch Motion: Glean’s team, including engineers, CSMs, and AEs, got hands-on during the pre-sales phase. They provided white-glove service to prove the product’s value.
- Building Trust: Lauren emphasized the importance of technical trust and executive alignment. “We learned alongside our customers, focusing on their true success criteria,” she said.
The Evolution: From High-Touch to Scalable Success
As Glean grew, the high-touch approach became unsustainable. The team had a Slack channel for every customer, with everyone from engineers to co-founders jumping in to help.
“It was breaking for us and our customers,” Lauren admitted. “We had to get creative.”
The Solution: Community-Led Customer Success
- Deprecating 50+ Slack Channels: Glean consolidated customer communication into a single Slack channel where customers could help each other.
- Customer Champions: Customers like Matt Mangia, an AI Builder Champion, began answering questions and sharing use cases, creating a self-sustaining community.
Pro Tip: “Community-led success isn’t just scalable—it builds deeper engagement and trust,” Lauren said.
Security and Trust: The Non-Negotiables
For enterprise customers, security is a top priority. Glean focused on delivering powerful messaging around data security and permissions early in the sales cycle.
Key Wins:
- Collaborating with Customers: When a large security company raised concerns about data governance, Glean worked with them to build new features, turning a potential deal-breaker into a competitive advantage.
- Building a Security-First Culture: AJ highlighted the importance of aligning company culture with customer values. “Trust isn’t just about the product—it’s about how you operate as a company,” he said.
Company Culture: The Secret Sauce
AJ and Lauren emphasized that culture has been a critical driver of Glean’s success.
Key Values:
- Make It Better, Make It Together: Glean’s culture thrives on collaborative tension—challenging each other to improve while working as a team.
- Hiring for Change: “We look for people who are comfortable with change and can think creatively,” AJ said. “Early-stage companies are unpredictable, and you need team members who can adapt.”
Pro Tip: “Take time to have fun and connect as a team,” Lauren added. “We have a Slack channel for selfies and celebrations—it keeps the energy high.”
Scaling Sales and CS: Rules of Engagement
As Glean grew, the relationship between Sales and CS had to evolve.
Key Strategies:
- Centralized Leadership: Having AJ oversee both Sales and CS ensured alignment and smoother handoffs.
- Multi-Threading: Glean incentivized CSMs and AEs to build relationships with multiple stakeholders at each customer. “We track multi-threading in Salesforce and offer spiffs for the most meetings,” Lauren shared.
- Executive Alignment: “A champion isn’t enough,” AJ said. “You need at least three executive contacts to mitigate risk if a champion leaves.”
Prioritizing Customer Success: Everyone’s Job
At Glean, customer success is everyone’s priority.
Key Initiatives:
- Celebrating Wins: Glean has a dedicated Slack channel for sharing customer success stories.
- Hands-On Support: Even as the company scaled, Glean maintained a focus on providing hands-on support during onboarding and beyond.
Pro Tip: “Create a customer success channel if you don’t have one,” Lauren advised. “It’s a great way to celebrate wins and keep the team motivated.”
Q&A: Key Takeaways
During the Q&A, AJ and Lauren shared additional insights:
- AI Transformation: Successful companies have a dedicated AI strategy team reporting to the CEO.
- Scaling Onboarding: Focus on multi-threading and involve Sales if a champion drops off during onboarding.
- Building Trust: Security and culture are non-negotiable for earning customer trust.
Final Thought: Sustainable Growth is a Marathon
AJ closed with a reminder: “Growth is exciting, but it’s a marathon, not a sprint. Stay focused on sustainable growth, and never lose sight of your ‘why.’”
