Conversation with Trello’s Stella Garber on SaaS Marketing, Scaling, and Remote Teams

I recently sat down with serial entrepreneur, marketer, and startup executive Stella Garber to discuss her experience as a startup founder, as well as her time leading marketing for Trello before, during, and after its acquisition by Atlassian in 2017. Our conversation touched on marketing strategy and tactics, the blurred border between product and marketing, scaling a team and the frameworks it necessitates, and managing a remote team. Read highlights from our conversation below.

Founder vs. Marketer

The majority of her career, Stella has held one of three roles: startup co-founder, sole marketing person on a scaling team, or marketing executive. Her experience at each affects her actions and strategies at the others. As CEO and co-founder at Matchist, Stella had to maintain a 10,000-foot view of every aspect of the business, choosing specific areas in which to dive more deeply. Later, as VP of marketing at Trello, Stella still maintained a broad-facing view of all marketing operations, but there was less to worry about and fewer aspects of the business she had to strategically neglect. To hear her tell it, she had an easier time sleeping at night as head of marketing than CEO.

Bucking Trends – Trello Marketing Strategy

Stella seemed to avoid the conventional wisdom of how to market a business software product like Trello at every turn. For one, she’s skeptical of the separation of product and marketing that many startups practice. She believes marketing represents the voice of the customer, providing integral feedback so the product team can design the software with end-users in mind. She also considered what additional education users would need with each incremental product change – whether they be blog posts, user guides, or product demos.

Stella’s vision began to take shape, and Trello attracted a cult following as its user-base grew. She attributed Trello’s early customers’ devotion to another strategy deviation from most business software products: she didn’t spend significant marketing dollars on paid ads. Instead, she focused on building the brand promise and consistency, ensuring that, simply, the product could do what users needed it to. Stella also eschewed building out multiple personas to represent the different possible end-users of Trello and strove to keep the product as broad as possible. She and her team built the tool to “organize anything with anyone.”

Although Trello is functionally both a B2C and B2B tool – employees are the true end-users, and often the buying decision is made by a business on behalf of its employees – Stella marketed to these two groups in very similar ways. She focused Trello’s messaging on organization, ease of integration, and positive disruption in workflows, all challenges that arise whether you are situated in a company or organizing a personal project.

These divergences from the norm of business software marketing paid off – since users weren’t pigeonholed into specific use cases, they began to use Trello to perform multiple functions across their professional and personal lives, including ones Stella never anticipated. One Apple employee and early user enthusiastically told Stella that she was using Trello for everything inside and outside of the office – including her PTA meetings and planning her child’s birthday party.

As Trello’s user-base grew, the team grew with it. Stella and I discussed how scaling affected her processes and workflow.

Building Processes while Remaining Agile

When Stella joined Trello, it had roughly 15 employees and its processes were limited to quarterly leadership offsites and yearly planning. At around 50 employees, Stella identified an inflection point, and the Trello team added a layer of process, including quarterly planning and press relations to both tell their story and coordinate launch timelines. At this point, Stella implemented the Objectives and Key Results (OKR) framework on her marketing team. But Trello didn’t implement company-wide OKRs until about the 100-employee mark – another inflection point.

The point at which founders introduce processes like the OKR framework to their teams is highly correlated with their personalities, Stella said. Because CEO Michael Pryor was more of a fluid leader who didn’t naturally implement processes, Trello’s culture also developed to be more agile. This directly conflicted with Stella’s type-A personality, however: she organizes and plans in both her personal and professional life, hence incorporating the OKR framework much earlier than Pryor. This led to a healthy dynamic wherein Trello – like many early-stage startups – vacillated between not enough and too much process.

Another interesting feature of Trello’s culture beginning to scale was that the team was largely remote, introducing a set of uniquely modern challenges: how to best utilize technology to maintain a strong company culture across a virtual team.

Building Culture on a Remote Team

Trello built a largely remote team, and Stella pushed back against traditional notions of commuting and office culture. She’s all too familiar with trying to work on a self-contained project in a traditional office setting and continually getting sidetracked by distracting coworkers, conversations, and interruptions. When Trello reached the 100-employee inflection point, about two-thirds of its team was remote. Stella says that this is a feature, not a bug, of Trello’s culture: a virtual team makes it easier to hire talented people, lowers employee attrition (thanks to inherent trust in employees and the perk of working from anywhere), and increases productivity.

Stella also incorporated “tools to mimic what happens in a physical office digitally” to ensure strong team dynamics at Trello. She built a #watercoolerchat channel on Slack for general chatter, used Zoom’s breakout room feature to randomly group 5-6 employees into video chat rooms, and held bi-weekly virtual “jam sessions” with beer and corny “icebreaker” games.

Stella sees Trello’s remote team as an asset, and has created a team-building model for today’s virtual teams.

General marketing and career advice

Stella peppered our interview with helpful pieces of advice for aspiring founders and young marketers. She warned against trying to do too much, as well as declaring a project or channel a failure before giving adequate time to bear results and make adjustments.

She also gave her younger self some broad advice that others may do well to heed:

Chill out. When you’re high-achieving and have a lot of goals, things never seem to move fast enough… But success takes a long time, a lot of building relationships, and a lot of trust. Give yourself time to breathe without putting on all this pressure.

Stella is head of marketing at Trello and advisor to Origin’s portfolio companies. She works remotely from her Chicago home office. Listen to our full interview on SoundCloud and iTunes.