How Upwind Reps Save 80% of their Day with Revenue Agents

Upwind is consolidating their tech stack for the AI era.

“Everyone's tech stack is changing right now,” Candace said. “We're at the point where we have the opportunities to choose tools that we actually think are going to move the needle, instead of being stuck with the tools that we are told that we need.”

Why? Candace Hopkins, Upwind's Senior Revenue Operations Manager, watched her star rep, Nico Prestipino, lose his day to his tech stack.

For Nico, reaching a single prospect took six separate tools:

1. Salesforce: He pulled his top thirty accounts for the week, ranking them by firmographic and intent scores.

2. LinkedIn: He tracked down the right contact at each account.

3. Enrichment: He found and pulled their email.

4. Claude: He moved into an agent he built himself to draft the emails.

5. Gmail: He pasted them in and pressed send for each one.

6. Calendar: He logged a follow-up task on his calendar by hand.

"You can just imagine his calendar," Candace said, "and the mental fatigue that a rep experiences without having a tool to help them really tie all these together."

With Rox, outbound prospecting collapsed into one tool. The source of truth, Salesforce, feeds into Rox automatically, so Nico doesn’t have to reference it himself. He logs in and starts outreach immediately.

“Within the first hour of onboarding him into Rox, it was like, ‘we just saved you 80% of your day,’” Candace said.

The Playbook

Upwind just wrapped its “best quarter yet.” Here are Candace’s rules for building an AI-powered GTM function:

• Reps adopt outcomes, not tools: a tool needs prove its value early

• Fix the data before you build: if the data is dirty, the agent hands your team wrong answers. And always back up your data, because an agent “can destroy records at a machine’s pace.”

• Prioritize governance: set guardrails on credits and tokens up front so reps can move freely without racking up costs.

• Build only what you can build efficiently: buy what could take months to build, test, and maintain

When to Buy + Build

“All over LinkedIn, everybody wants to build their own tool,” Candace said. But building also involves costs and upkeep.

“If an operations leader came to me and asked what I would recommend they do first in building their own AI infrastructure tool, I would say don't even start,” Candace said.

She said to clean the data first. “The building an AI is the easy part…What that agent and that tool will rely on is your initial infrastructure.”

Tools that took months to stand up and manage when built internally, Candace outsourced. "If it takes us two months to build a tool and then have to maintain it, versus buying a tool that's already built, already tested, something we can just plug and play, it's a no-brainer," she said.

Can you skip Governance?

For Candace, “governance is a top priority,” whenever a tool is built, launched, or adopted. Her goal is to keep reps within clear limits while still giving them the freedom to move fast and generate pipeline.

How much work governance takes depends on the tool. With Claude, she has to write the guardrails herself. "You have to build a file and then type in that file, and then you reiterate whenever it goes haywire," she said. “So it's this constant monitoring and tweaking versus a tool like Rox, where it’s already built for you, and all you have to do is click a little button, and you can trust it.”

A Builder’s Mindset

Candace's instinct for building started early. She grew up in Mildred, Texas, a rural town outside Dallas, with a graduating class of 52 students.

"Something that I would do to just defeat boredom was go out to the shop and take apart anything I could, build things," she said. She connected that curiosity to her work in operations today, solving problems, stopping leakage, and improving systems.

She explained how her team supports the sales motion: "A salesperson is driving a car, and revenue operations and go-to-market engineering is building the engine that makes that car run," she said. "We’re not only just building the engine now. Now we are designing and launching the self-driving mode of that car."