How smarter training and territory planning drives Outreach adoption

The best sales tools are only as powerful as the people using them. Yet for many RevOps and Enablement teams, sales tool adoption (or, lack thereof) is the silent killer of ROI. We might be a little biased, but Outreach’s sales execution platform is one of the most powerful platforms on the market, however its effectiveness depends entirely on how well it’s rolled out and adopted by reps. The challenge isn’t what the tool can do—it’s how well it fits into daily sales workflows. 

In a session at our annual sales conference, Unleash 2025, Liz Chavez (Senior Director of Revenue Enablement) and Ashlie Ketteman (Director of Revenue Operations) of SpyCloud shared how they reversed low adoption through collaborative territory planning, rep-centric onboarding, and targeted coaching. 

As a cybersecurity provider for Fortune 500 companies and government agencies, SpyCloud’s sales motion can be long, complex, and highly regulated. After rolling out Outreach, they hit early roadblocks: low login rates, zero call recordings, and reps clinging to old tools like Apple Mail — missing out on critical data and insights to help move their conversations and deals further. With a few simple but strategic changes, like territory planning, rep-centric onboarding, and targeted coaching, things began to turn around. 

The results? 

• 56% increase in call recording usage 

• Meeting type tagging jumped from 3% to 50% 

• Reps began closing deals in under 90 days 

Here’s how they did it — and what your team can learn from their journey. 

Diagnosing the Real Adoption Problem 

Adoption issues don’t always wave a red flag. They tend to show up as smaller, tactical breakdowns: inconsistent data, unlogged activity, poor usage of features like sequences or call recordings. But those are symptoms, not root causes. At SpyCloud, the real issue ran deeper. The root cause was cultural. Sellers saw Outreach as a transactional tool designed for SDRs, not a strategic asset that supported the entire deal cycle. 

Ketteman, a longtime Outreach user, described early friction: “We saw very few call recordings, very few logins. It was very clear from the get-go that Outreach was not baked into our sales mission.” 

Even Chavez, who was new to Outreach at the time, wasn’t sure how to get traction until she and Ashlie began collaborating to embed Outreach into rep’s onboarding workflows. Sales reps worked not only in Outreach, but also their Gmail inbox, their calendars, and other tools like Salesforce. (A simple solution with Outreach Everywhere Chrome extension.) 

Still, Outreach was competing for attention and not complementing existing habits. The fix wasn't more training. It was reframing the tool’s value, both operationally and strategically. 

Rebuilding onboarding around the rep 

To boost Outreach adoption, SpyCloud started by reworking their training and onboarding to match how reps actually learn — gradually, in context, and with the right support. SpyCloud broke Outreach onboarding into three thoughtful layers, each building on the last: 

1. Outreach University for initial setup and platform basics 

2. Live enablement sessions with Chavez to walk through everyday workflows 

3. Follow-up coaching with Ketteman to dive deeper into account views, reporting logic, and real-world application 

They also launched a quarterly training series held in small team meetings (coined by the duo as the “Ashlie & Liz Roadshow”). Each session covered one or two specific workflows — not full platform walk-throughs, but real use cases like identifying stale accounts or tracking email engagement. 

While Call recordings were also a critical resource to glean learnings from, SpyCloud’s reps were skeptical of recording their customer calls, especially working in an industry like cybersecurity, where privacy is paramount.   

Chavez and Ketteman tackled those concerns head-on. They emphasized how the platform asks call attendees for consent, showed the value of recordings for onboarding and coaching, and most importantly, celebrated every win. 

“We would literally shout people out for recording a call,” said Chavez. “Even if it was just one five-minute meeting, we celebrated it.” 

Outreach adoption metrics began to climb, and eventually reps started asking how to do even more with it.  

Operationalizing the metrics that matter 

To gauge the effectiveness of their user engagement strategies, SpyCloud built their approach around four core Outreach adoption metrics: 

• Account-level engagement 

• Email activity (volume, reply, bounce) 

• Meeting types 

• Call recordings 

Each of these metrics tied directly to rep workflows and pipeline health. Low email volume? Might be a Salesforce connection issue — or a signal to check enablement. Multiple discovery calls in on deal? That’s a cue to revisit alignment with buyer needs. High bounce rate? That’s a list hygiene issue hiding as underperformance. 

“Email activity is such a great indicator,” Ketteman explains. “If sends are down, we ask: Is Outreach connected correctly? Are you using the right email client? Are contacts even in Salesforce?” 

Instead of relying on manager audits, SpyCloud made metrics transparent and gamified the process. They created dashboards that showed which reps had the highest reply rates, who logged the most meetings, and who had the highest bounce rate. 

But those usage tracking insights didn’t live in static dashboards or stale reports. They came to life in real conversations. As Ketteman noted: “The goal wasn’t to say, ‘You’re doing it wrong.’ It was to say, ‘Tell us about your workflow. Let’s get it working for you.’”  By treating data as a coaching asset rather than a compliance tool, SpyCloud changed how reps viewed their work and how fast they ramped up. 

Territory planning as the turning point 

Perhaps most impactful of all, Chavez and Ketteman discovered a new way to get seller buy-in that went beyond changing workflows — they started changing ownership. SpyCloud replaced static, top-down territory planning with collaborative scenario planning tools that let reps reverse-engineer success based on their own pipeline realities. 

With this new tool, reps could go through the exercise of adjusting conversion rates and average deal sizes to see how many opportunities they needed to hit quota.  

Then, using their actual Outreach engagement metrics, they mapped backward to determine how many emails, meetings, and calls that would require.  

“When reps are co-creating their territory plans and you're giving them the information to make informed choices about what their plan looks like for the year, it just automatically increases engagement and accountability,” Chavez said. 

To keep plans active, SpyCloud launched territory planning Slack channels. These dedicated spaces included the rep, manager, and both RevOps and Enablement stakeholders. Every week, reps received a snapshot of their metrics directly from Ketteman, along with updates about new Outreach features, workflows, or enablement resources. This made metrics visible and action-oriented. 

Building a culture of coaching 

SpyCloud shifted from reactive enablement to something much more impactful: a coaching-first culture. When a rep’s numbers dipped, the team didn’t assume disengagement — they assumed misalignment, and leaned in to help. 

“When a rep’s numbers looked off, my response wasn’t ‘Fix it,’” Ketteman said. “It was ‘Let’s hop on a quick screen share and figure it out together.’” 

This mindset extended into onboarding, too. One new sales engineer remarked after their first team call, “I feel like I know all of you already. I’ve watched so many of your call recordings.” That moment made it clear to Chavez that Outreach had become woven into the team’s daily rhythm. 

The impact didn’t stop with Sales. Outreach usage became so visible and valuable that other departments took notice. SpyCloud’s Customer Success team asked to join the platform. Even HR group expressed interest in using call recordings for onboarding and training. Adoption had become contagious. 

Strategy drives adoption, not features 

SpyCloud’s results weren’t driven by adding more tools or enforcing stricter rules. They came from strategic alignment — giving reps ownership of their workflows and showing them how Outreach could help them hit their number. 

“By changing our messaging and meeting reps within their workflow, we increased adoption metrics like crazy,” said Chavez. 

Here’s what other RevOps and Enablement teams can take away: 

• Train in layers, not lectures: Onboarding should reflect real workflows. Start with setup, reinforce with live sessions, and follow up with contextual coaching. 

• Measure what matters: Look beyond activity volume. Track metrics like call recordings, reply rates, and meeting types. 

• Make coaching the goal: Use adoption data to open doors for support — not just to flag issues. 

• Plan territories together: Let reps reverse-engineer their goals using real, accessible data. 

• Keep plans flexible: Use internal communication channels like Slack, shared dashboards, or scenario templates to make planning collaborative and continuous. 

When adoption is tied to strategy — and strategy is centered on the rep — tools like Outreach become essential.