The Hard Way Pays Off: Inside Sierra’s Design Partner Strategy

Instead of chasing low-friction pilots, Sierra asked design partners to pay, commit time and co-build — converting 100% of these partners into customers.

Finding the right partners: Define your criteria

Sierra didn't yet have an ideal customer profile — that's some of what the design partner program would eventually validate, so they cast a wide net. With the goal of landing four, the team came up with a list of 40 potential partners (some friends, some strangers). Here’s the criteria for how they selected these companies:

Criteria #1: Horizontal appeal

Many successful startups have gotten early traction selling to other tech companies. And it likely would’ve been easy for this founding team — with decades of connections as founders and executives across tech giants — to follow that same playbook.

“But we believed AI would transform the customer experience across every industry, and we wanted to validate that theory. So we went to people in healthcare, CPG, media, retail and tech without knowing yet which ones it would actually resonate with,” says Randolph.

Criteria #2: Large scale

Sierra’s early story is another reminder of how quickly AI adoption has accelerated. “We started with the pitch: You should use AI for customer service — which was actually non-obvious a few years ago,” says Randolph. “We wanted design partners that had to consider the risks associated with AI seriously, as we learned a lot from mitigating these risks together.”

Criteria #3: Real problems

No matter the size of the company, Sierra wanted to avoid AI tourism. “In some conversations it became clear that prospective partners were interested in ‘playing with AI’ and building internal prototypes,” said Randolph. “We wanted customers who wanted to solve a real problem that meaningfully impacted their business.”

Criteria #4: Not too many friendlies

Sierra had an advantage in that their founders had huge networks. But finding design partners who weren’t warm intros was important to validating Sierra’s thesis.

Approaching partners: Beware the frictionless gap

"A lot of startups will say to prospective partners, 'We just need a few hours of your time each month.’ But you need mutual investment and risk,” says Randolph.

Structuring the partnership: Mutually assured construction

Payments

Putting up hurdles for early customers to jump through sounds like the opposite of Silicon Valley’s “move fast” ethos — but in Sierra’s case, it helped them disqualify companies they felt were AI tourists. “Everyone’s excited to experiment with AI. So the financial commitment had to be significant enough that people really needed to think about it, get approval from their boss and go through the procurement process,” says Randolph.

Time limits

“Whatever you do, don’t allow the ‘try this and give us feedback when you are ready’ approach because they will say ‘Ok cool, we’re excited to work together, and we’ll get you resources next month,’” Randolph says.

Running the program: Build trust through rapid iteration

Kickoff meeting

Randolph recommends starting with a service engineering discovery session, a 60-90-minute meeting with the whole team. He had four main goals coming out of each kick-off meeting:

• Agree on the three or four main problems to solve. One company wanted an AI agent to do returns, exchanges and package tracking. For another, it was having the agent solve connectivity issues.
• Define swimlanes. “We needed clear accountability for who owns the customer experience and who owns the technical integrations,” he says.
• Commit to a real launch during the partnership, not a prototype. Randolph suggests getting a commitment upfront from the customer that this isn't just something for them to tinker with.
• Create ongoing touchpoints to avoid “out of sight, out of mind.” Randolph made sure to establish a standing meeting and a Slack or Teams channel to open a constant line of communication with the partner.

Weekly iteration and communication

“We would try to get the first version of the agent built within two weeks. Even if it was bad, it was something,” said Randolph. These minimum viable agents were quite simple — for example, if the company wanted the agent to do exchanges, the MVP might just answer questions about exchanges from the help center.

Prioritizing what to build

When it comes to design partners, choppy waters can throw your boat off course. How do you resolve the needs of multiple VIP customers when they don’t always align? It sounds like an enormously complex problem. But Randolph keeps it simple: “Anchor everything on the core problem. If the design partner’s request goes towards that core problem, then we’ll do it. If it’s not, then we won’t,” he says.

Rally internally around a milestone

Behind the scenes at Sierra, they were ruthlessly obsessed with one particular milestone: “We would pick a launch date when the agent would be deployed,” Randolph says. To get there, the team working on design partnerships had internal weekly syncs where they’d continually ask three questions:

• What do we need?
• What do they need?
• Are we on track with the launch date?

Wrapping up: The path less trodden

Running an impactful design partner program is extremely difficult — teams are on call at every moment, desperately trying to keep up with partner requests, a treadmill that never seems to stop. But it’s also a period of intense closeness to customers that has a certain magic at the earliest stages. “It was a shared experience that built customer empathy across Sierra. After engineers left their dedicated design partner post, they would look back and think fondly of that time working so closely with them,” says Randolph.

And the proof in Sierra’s approach goes much deeper than a 100% partner-to-customer conversion. “Champions at our customers have gotten promoted because we solved a problem for them that was so core to their business. We’ve had multiple design partners mention us on their earnings calls. They’re still among our most trusted collaborators and critical to the success and authenticity of Sierra,” says Randolph.