Sales Capacity Planning That Doesn’t Suck (Jenny Dingus, SVP Global Sales @ Clio)
Why Your Annual Plan Is Already Broken (And What Elite Leaders Do Instead)
I have a confession: Until a few years ago, I built my annual revenue plan the same way most of you probably still do.
Open the spreadsheet. Calculate total ARR target. Divide by average rep quota. Add 20% for inevitable attrition. Multiply by cost per head. Present to board. Get funding. Start hiring.
The model is seductively simple: **People x Quota = Revenue**. It’s what every SaaS playbook teaches. It’s what investors expect. And according to Jenny Dingus, SVP of Global Sales at Clio, it’s fundamentally broken.
Jenny joined me on the Revenue Leadership Podcast fresh off leading Clio through one of the most complex periods in the company’s history: launching multiple new products, orchestrating a billion-dollar acquisition of VLEX, and completely reimagining how a $5B legal tech platform thinks about revenue growth. What she shared challenges everything we’ve been taught about scaling revenue organizations.
Clio just raised a $500M Series G and serves over 150,000 legal professionals globally. Jenny’s spent the last few years proving that the traditional capacity planning model doesn’t work in vertical SaaS and building something better in its place.
Here are the five most valuable frameworks from our conversation.
1. The Integrated Planning Framework: Beyond Linear Capacity
Most revenue leaders are still building plans on a dangerous assumption: that hiring more sellers creates proportional revenue growth. Jenny’s watching this model collapse in real-time, especially in vertical markets.
“You need pipeline, you need market opportunity,” Jenny explained. “You can add headcount all the time but it’s not everything. Headcount alone and brute force is not a sustainable way.”
The problem goes beyond philosophy. Research from [SaaStr](https://www.saastr.com/) shows that rep productivity has declined 30% since 2020, meaning the historical relationship between headcount and output has fundamentally shifted. When productivity degrades faster than you can hire, you’re running on a treadmill that’s speeding up.
Why we still do it: “It’s easy on a spreadsheet,” Jenny said with a laugh. “You need a plan to stress test, but the functions at the center of the planning exercise aren’t operating.”
Jenny’s alternative treats headcount as one growth lever among many.
Jenny’s Integrated Planning Framework replaces the linear model with four parallel growth engines:
1. Pipeline Engineering
“What are all the channels?” Jenny asks. This means forensically understanding every source of qualified pipeline and how they interact. At Clio, this meant spending significant time collaborating with marketing to understand volume, velocity and conversion by channel.
2. Monetization & Pricing Strategy
“Balance market penetration and value capture,” Jenny noted. Clio launched multiple new products while simultaneously running “a big monetization effort.” The key: You can’t set quotas until you understand attach rates and pricing implications. Too many leaders treat pricing as static when it should be a quarterly conversation.
3. Market Expansion
This includes new segments (Clio just launched enterprise), new geographies, and crucially, knowing when to bake them into the plan. “Bake them in conservatively,” Jenny advised. They’re not planning for the full year on new products, just Q1. “This will give us the opportunity to collect enough data to plan for the rest of the year.”
4. Strategic Partnerships
Jenny means systematic channel development and ecosystem plays that create compounding returns, not vanity partnerships that look good in press releases.
The shift in thinking: You’re asking “What’s the optimal mix of growth levers, and what capacity do I need to service the demand they generate?” instead of “How many reps do I need?”
2. Confidence Intervals Replace Annual Commitments
Here’s where Jenny’s approach gets really interesting and really different from conventional wisdom.
For Clio’s new product launches, they’re not forecasting 12 months out. They’re planning in quarters with explicit confidence intervals.
“We’re not planning for the whole year right now, just planning for Q1,” Jenny explained. “Not in the habit of replanning. Not a lot of appetite to complain about targets.”
This approach borrows from Bayesian statistics and product management: update your priors as you learn. [Annie Duke writes about this](https://www.annieduke.com/) extensively in *Thinking in Bets*, noting that the best decision-makers constantly update their confidence based on new information rather than defending initial predictions.
At Clio, they meet multiple times per week to review early data from new product launches. “This informs enablement, marketing spend, resource allocation,” Jenny said. With new products specifically, “They’re watching it minute by minute and making adjustments.”
The sophistication here: They’re distinguishing between Business As Usual performance (where annual planning makes sense) and New/Emerging opportunities (where quarterly learning cycles matter more).
**Why this matters:** When you commit to rigid annual plans in uncertain environments, you create organizational antibodies against the very learning you need. Teams hide bad news. Managers sandbag. Everyone games the forecast instead of learning from reality.
3. The “Draw the Owl” Integration Playbook
When Clio decided to acquire VLEX mid-summer with plans to launch at ClioCloud Conference in mid-October, Jenny faced a systems integration challenge that would break most sales organizations.
She needed to build systems, enable sellers, integrate products, and create new go-to-market motions while running the existing business. Her team’s execution offers a masterclass in change management at speed.
The name comes from Clio’s company value: “Draw the Owl,” inspired by that old meme showing two steps: 1) Draw two circles, 2) Draw the rest of the owl. It’s about empowering teams to figure things out creatively rather than waiting for perfect instructions.
The Operating Structure:
Jenny broke the integration into 5 key workstreams, each with dedicated owners and resourced teams (some with 30-40 people):
Monetization strategy
People & org design
Sales readiness
Systems integration
Go-to-market execution
Critical detail: They asked leaders to spend 70% of their time on integration. “We’re pausing everything and all their weight went into it,” Jenny said. No half measures. No “do this on the side.”
The Communication Cadence:
Most acquisitions fail on communication. Clio succeeded by treating messaging as a system:
1. Consistency at scale
“5 times, 5 different ways,” Jenny emphasized. This follows the Rule of 7 from marketing psychology: people need to hear something 7 times before it sticks.
2. More importantly than hearing it, they have to feel it
Jenny’s team didn’t just *tell* people about new products. They put sophisticated demo environments in sellers’ hands so they could experience the customer impact firsthand.
3. Weekly all-hands
Still running with dedicated teams. “Constantly reinforcing what they’re focused on. Sharing information in real time.”
The psychological principle: When organizational change creates uncertainty, human brains default to threat response. The antidote? More *predictable* information. Weekly cadences create rhythm. Rhythm creates safety. Safety enables performance.
4. Enablement as Continuous Loop, Not Launch Event
“Biggest learning: enablement doesn’t stop when you launch,” Jenny said. “That’s the starting point.”
Most companies treat product launches like military campaigns: build up to the big day, then move on. Jenny’s team built a continuous learning system instead.
The Feedback Architecture:
Centralized Slack channels where sellers ask questions without judgment
Weekly synthesis of themes and questions
Cross-functional tiger team (product, PMM, enablement) reviews weekly
New assets and training created based on actual field friction
The Enablement Toolkit:
Newsletter of the Week - Curated weekly digest of the most important information for sellers
Meeting in a Box - Pre-packaged slides and exercises managers can use in team meetings
AI Sales Sim - Custom bots for practice (right place, right time for their launch)
This mirrors the concept of deliberate practice from Anders Ericsson’s research. Learning doesn’t come from exposure. It comes from repeated retrieval and application with feedback loops.
**What makes this different:** Most organizations have “knowledge bases” that become graveyards. Jenny’s system is *active*. It pulls questions from the field, synthesizes patterns, and pushes refined answers back out weekly. Think of it as a learning flywheel rather than a library.
5. Humility as Competitive Advantage
In our quickfire segment, I asked Jenny what separates good CROs from exceptional ones. Her answer surprised me:
“Humility is a really important quality. Especially right now with everything changing so much. Stay curious and humble and create space to learn not only from market trends, but from our people and from our customers.”
Jenny’s articulating something deeper about decision-making in uncertainty. This connects to Julia Galef’s concept of “scout mindset” versus “soldier mindset.” Soldiers defend positions. Scouts explore terrain. When you’re navigating unprecedented market conditions (AI disruption, efficiency expectations, vertical market constraints), scout mindset wins.
Jenny’s specific advice to new leaders:
“Irrespective of what somebody’s title is, their experience, their tenure, don’t assume they have all the answers. Leaders are looking for the experts in the field to help them form an opinion. If you happen to be in the room for a conversation, you’re there for a reason. Make sure that you’re contributing in a meaningful way.”
This connects to psychological safety research from Amy Edmondson at Harvard. Teams with higher psychological safety make better decisions because information flows more freely. They don’t just feel better.
The counterintuitive insight: Most executives think certainty projects confidence. Jenny argues the opposite. Intellectual humility creates more space for the organization to surface problems early when they’re still solvable.
The Happiness Advantage: Why Optimism Compounds
When I asked Jenny about the best thing she’d read recently, she immediately cited The Happiness Advantage* by Shawn Achor: “His thesis is that happiness fuels success and not the other way around.”
Achor’s research at Harvard showed that positive brains have a 31% higher productivity than negative, neutral, or stressed brains. Sales improve 37%. Accuracy on tasks improves 19%.
The mechanism: When you’re in a positive state, your brain releases dopamine. This doesn’t just make you feel good. It activates the learning centers in your brain. You literally get smarter when you’re happy.
Why this matters for revenue leaders: You can’t out-process your way to exceptional performance if your team is operating from a stressed, threat-response state. The “grind culture” so prevalent in sales doesn’t just burn people out. It makes them objectively worse at complex problem-solving.