How Warmly Helped Their AE Manage 40% More Pipeline (Without Losing Their Best Rep)

Meet Warmly

Warmly went from $100k to $7M ARR in under 3 years. 🤯

The problem? Their sales team was drowning in manual admin work – CRM updates, follow-ups, the works.

Reps were spending 1.5hrs a day updating HubSpot fields, sales-to-CS handoffs slipping through the cracks, and top performers were burning out, with one nearly leaving for a higher-paying role.

Meanwhile, with a year and a half of recordings trapped in Fathom, Warmly's CRO (Keegan Otter) had no way to coach reps shy of bingeing call recordings.

Here's four shifts the Warmly team made with Sybill:

• From admin overload to getting 2-3 hours back
• From nearly losing reps to 2+ year tenure
• From overworked AEs to 32% more demos per day
• From CROs and managers bingeing calls to coaching in real time.

Oh, and along the way they crushed their revenue goals, crossing $7M in ARR.

Below we’ll cover these four shifts and what we learn from them. 👇

From admin overload to getting 2-3 hours back.

Before onboarding Sybill, Warmly reps kept a 1-2hr calendar block for admin work every. single. day. They'd use this time for CRM updates, follow-ups, deal strategy, CS handoffs, and more.

With Sybill, they:

• Automated their HubSpot CRM updates, so deals were updated every time reps hung up or hit send. 90+% of the 15-20 fields per deal—MEDDIC, pain points, next steps, competition—auto-filled without reps lifting a finger.
• Automated email follow-ups, drafting them in their reps' tone of voice after every call. The result? An 88% open rate across thousands of sends, with personalized recaps for each stakeholder (marketing gets marketing pain points, CEOs get CEO-level recaps).
• Eliminated sales-to-CS handoffs entirely. Before Sybill, every account transition required a 15-minute sync call where context inevitably got lost. Now, CS team members simply query Sybill to pull up a customer’s complete history—1.5 years of calls, emails, and context—in seconds. No handoff meeting required.

And those freed-up calendar blocks? Gone. Reps removed them entirely because the work simply didn't exist anymore.

From overworked AEs to 32% more demos per day.

All that admin work slowed down how many deals each rep could handle. Less active deals means decreased deal flow and fewer opportunities to hit quota.

With 2-3 hours back in their day, Warmly reps started taking more meetings. A lot more.

Reps started handling 1-2 additional demos per day—a 25-32% increase in deal flow. And they did it without working longer hours or burning out.

But here's the kicker: more demos didn't mean lower quality. Warmly maintained their 27-35% win rate throughout (some months hitting above 30%). The process that was already working (their follow-up sequences, MEDDIC qualification, multi-stakeholder engagement) now happened faster and more consistently.

Why? Because Sybill eliminated the bottleneck. Reps weren't choosing between taking another demo or getting their pipeline updated. They could do both.

From nearly losing reps to 2+ year tenure.

During Sybill's trial period, Warmly almost lost one of their top performers to a higher-paying job offer.

This wasn't just any rep: she had come from 6Sense and was a senior performer.  Another company was trying to poach her with better compensation.

Keegan sat down with her and asked what it would take to stay. Her answer surprised him:

It wasn't about money. It was about her day-to-day life as a rep.

Keegan made the call to fully adopt Sybill. The rep stayed. And she didn't just stay—she went on to win Warmly's sales competition for most closed won revenue, taking home a Tesla in the process.

The broader impact? Every AE on Warmly's team has now stayed beyond the industry average tenure of 1 year, 2 months. Their most senior reps are at 1.5-2+ years and counting. In an industry where burnout and churn are the norm, Warmly built a team that actually wants to stick around.

From bingeing calls to coaching in real time

Before Sybill, Keegan's coaching process was brutally time-consuming. To understand what was happening in deals, he'd have to:

• Manually review hours of call recordings
• Ask reps to walk him through their pipeline
• Dig through HubSpot to piece together deal health

With 16 GTM team members and dozens of active deals, it just wasn’t unsustainable.

That’s why the Sybill team migrated 1.5 years of Fathom calls into Sybill, so all of Warmly’s current and active deals were fully searchable.

This meant Keegan could ask questions across all of Warmly’s deals at once, like:

• "Show me deals where integration requests came up in the last 90 days and tie them to deal values."
• "Which closed-lost opportunities from last quarter have the strongest signals for re-engagement?"

Sybill would reply with an answer in seconds, including direct links to the relevant calls.

But the real breakthrough was in how this enabled real-time, targeted coaching.

Keegan started using Sybill to flag bad demos: calls missing qualification questions, next steps, or a clear economic buyer. So instead of spending hours reviewing recordings, he could scan Sybill's summaries, identify the coaching moment, and jump in with specific feedback.

He also started using Sybill to prepare for deal reviews. Before jumping on a call, he'd ask Sybill: "Tell me everything about this account." Within a few minutes, he was fully briefed, without slowing down his reps or lost time in prep.

Warmly managers adopted the same approach. They'd use Ask Sybill to identify:

• which deals were at risk,
• which reps needed support,
• and where the team was collectively missing opportunities.

Weekly pipeline reviews that used to take hours now took minutes.

Coaching moved from reactive ("let me listen to this call that already happened") to proactive ("let me identify patterns across 50 calls and coach to what actually matters").

The Hard Numbers

Okay, now that you know the whole story. Here’s the self-reported numbers of what Warmly did with Sybill.

Time savings:

• 10x faster post-call work: What took 2 hours now takes 10 minutes
• 2-3 hours saved per rep per day on manual CRM updates and admin work
• 90% of deals updated same day (vs. 48-72 hour delays before)

Deal flow:

• 25-32% increase in demos per rep per day (1-2 additional meetings)
• 27-35% win rate maintained throughout growth period
• $80K closed-lost deal revived using Sybill insights in first 45 days

CRM & data quality:

• 90+% automation rate for HubSpot field updates
• 15-20 fields auto-filled per deal (MEDDIC, pain points, next steps, competition)
• 88% email open rate on AI-generated follow-ups (vs. industry average)

Team retention:

• Full Sybill adoption across the 16-person GTM team
• All AEs retained beyond industry average of 1 year, 2 months
• 2+ year tenure for senior reps and counting
• Top performer stayed instead of leaving for higher-paying role

Summary

Warmly's reps were drowning in 1-2 hours of daily admin work. Top performers were burning out, and their CRO had no scalable way to coach the team.

With Sybill the Warmly team went…

• From admin overload to getting 2-3 hours back, automating CRM updates, follow-ups, handoffs and more.
• From nearly gone to 2+ year tenure, keeping their best reps well longer than the industry standard.
• From overworked to 32% more demos per day, with every rep taking on an extra 1-2 demos daily.

And Keegan from bingeing calls to coaching in real time. No more hours reviewing calls. Keegan can get answers across 1.5 years of conversation data in seconds—spotting at-risk deals and identifying coaching moments as they pop up.

Bottom line: Warmly gave their team time back, increased their tenure, increased rep capacity, and hit $7M ARR because they stopped making their best people do work Sybill could handle instead.