Introducing Olli: Your Next Sales Hire, Designed to Simplify Complex Deals & Make Your Team Wildly Successful

The data, but do you really need it?

We can start with the data. Like the fact every $1 of ARR (new logos + upsells + and renewals) costs 60% more in Sales & Marketing spend this year, than it did in 2021:

Or the fact that new logo win rates are hovering at 19%. 

Which means you need ~5.3X pipeline coverage to hit plan—a wildly expensive and difficult way to grow. Like how I’m constantly feeding my toddler organic, non-GMO blackberries to keep her growing. 

(I never budgeted for this.)

But I don’t think you need any more numbers than that. Because something’s changed in the past five years, and I think you can feel it. 

We all can.

It feels like we’re running on a treadmill, with some insane trainer who’s got their finger on the speed and incline buttons at the same time: 

I’m pretty tired… but slowing down means faceplanting onto moving sandpaper. That’s way worse.

Designing a sales-led GTM: choices & tradeoffs

Since the advent of ARR, revenue leaders have split their GTM strategy based on a choice. A tradeoff. Between two fundamentally different approaches:

• Account-Based: a tailored approach focused on a shortlist of target accounts.
  
  (The bet is high win rates + big ACV’s offset long cycles, and small account lists.)
  
  
• Scale: a volume-based approach, with a long list of accounts and one-sized sales stages.
  
  (The bet is a pipeline as fat as your uncle’s waistline and fast cycles offset small ACV’s.)

So, naturally, we segment our teams and process based on: 

• Key Accounts: a high-touch, high-conversion approach. Strategic reps pour gallons of time and creativity into a small handful of deals.
  
  
• Territories: everyone else gets the high-velocity, high-volume approach.

And you might be thinking, “What’s wrong with that? Hasn’t it always been that way?”

It has been. 

But should it be? 

Just look at your mid-market and commercial segments—where 11+ buyers are involved in getting to a decision—then tell those reps with a straight face they’re not doing “complex deals.” That because their ACV is “only” $50k - $75k, they shouldn’t do what strategic reps do: account research, points of view, business cases, tailored demos. That they can win 40%+ of their opps without any of that:

Stick to the script, swap the logos on the deck, copy/paste the email template. You’ll be fine.

And here’s the rub:

The extremes are pretty clear. Of course a 7-figure global enterprise deal and a $5,000 mom-and-pop shop are different. 

But what about the messy middle? The reps trapped between needing to tailor their activities, and needing to run fast to keep up with 15 - 20 active deals at once? 

Which is point #1 you need to know about Olli: 

Olli’s designed to let you treat every account, like a key account. No more tradeoffs.

Modeling “Rep Capacity” (and the rub)

In this write-up, I broke down the Sales Velocity equation to show what (in)effecient growth looks like, based on the typical spreadsheet: headcount, and productivity per rep. 

Now, here’s a slightly different way to look at Rep Capacity, which mirrors the breakout above: 

Rep Capacity = # Accounts  (x)  [ # Activities  (x)  Time/Activity ]  

Notice a few (semi-obvious) things here: 

1. Rep Capacity is fixed.
   
   Sure, reps could work 50 hours a week vs. 40. Lots of top reps do. But there’s still an absolute ceiling which makes this a pretty “fixed” variable in the equation.
   
   
2. The # of Accounts that reps can work decreases, if # of Activities per account increases:
   
   If you’re managing 12 vs. 2 buying contacts, well, that means more meetings, more prep, more follow-up. Plus more internal communication (e.g. sales engineers involved).
   
   
3. The # of Activities a rep can complete decreases, when the Time/Activity increases:
   
   Writing a business case obviously requires a lot more effort than plucking a template product deck off the shelf and hitting send, for example.

So what happens when you run out of Rep Capacity? 

Well, the two most popular options are:

1. Buy more capacity.
2. Cut out time-intensive activities.

But most CFO’s aren’t loving option #1 (buy more capacity) anymore. It means headcount, and headcount means $$$. 

The average AI agent is… well, pretty average

Which is why most teams turn to option #2 above (cut the time-intensive activties). Automating stuff, by hiring AI agents instead of humans. 

But most of this has largely been dabbling with AI "Level 1." Because what’s easiest to outsource to robot labor is the lowest-value work. 

The activities that move the revenue needle the least. 

Here’s the difference:

• Level 1: “How do we cram AI into our *existing* process?”
• Level 2: “How do we use AI to build the *right* process?”

Level 1 is just forcing AI into the same ol' process—no fundamental change in strategy. Same activities, just a bit more efficient. “Hey AI, fill in these CRM fields so I don’t have to.”

It’s a fine starting point. But Level 2 is what I find way more interesting:

“Can AI let us do what we needed, but *couldn’t* a year ago?”

For example:

• "Can our mid-market reps run deals with the same kind of thoughtful strategy as our key account reps? What would happen if they do?”
• "Can our reps do that while also increasing the # of active deals they manage at once?”

Point #2: Olli’s focused on the hard, high-value work.

Activities that are hardest to automate—and therefore, most likely to get left behind in a week—are Olli’s focus. Because these carry the highest “casual” relationship to win rate, ACV, and urgency.

Broken out by skillset, what often gets shortchanged (without Olli) are the thoughtful, tailored tasks:

1. Account Planning:

- Deep research to build a point of view with hard-to-find intel
- Writing forwardables to tag-team with executives on warm intro's
- Partnered with marketing to design ABM campaigns

2. Discovery:

- Isolating the root causes behind complex & long-standing problems
- Crafting metric trees to link workflow problems back to exec-level metrics
- Gap analysis to compare won/lost data with current deals to prioritize risks 

3. Multithreading:

- Assembled an effective buying committee with proactive outreach
- Designing the flow of internal communications with account maps
- Converting skeptics to build consensus in a group of 20+ buyers

4. Writing:

- Crafting problem statements that grab attention with customer data
- Co-creating messaging to enable champions during internal meetings
- Framing new internal projects to align with executive-level priorities

5. Collaboration:

- Collaborating with Sales Engineers to design demos that play like a movie
- Partnering with CS to address post-sale concerns and setup expansion
- Coordinating resources to build POC’s that convert on time

6. Project Management:

- Managing Mutual Action Plans to hit joint deadlines
- Navigating the SLIP maze: security legal, IT, procurement
- Accurately forecasting complex deals based on group behaviors

What I’m outlining isn’t exactly new information. 

This list typically gets baked into a playbook: a series of tasks broken down by stage, scripting out the “golden path.” A sequence of steps that, if done correctly and consistently, prints new ARR. 

It’ll often look something like this: 

So you can boil our job as revenue leaders down into two basic questions:

1. What % of deals in our pipeline match our playbook?
2. When deals do match, does sales velocity $ increase?

In short:

1. Adoption: “are we doing it?”
2. Impact: “does it work when we do it?”

There should be a WIDE gap in revenue between the reps that do vs. don’t adopt the playbook. (If not, the playbook’s off or outdated, and we’ll cover that second point in a minute.) 

Point #3: Closing the execution gap = Olli’s job description

Pause here for a minute:

What % of your deals have even a fraction of those activities happening? 

• Open a list of “Stage 3” deals. (Actually do this.)
• How many have an executive summary, tailored for that specific customer? 

30% of deals? More? Less? 10% of deals?

If you test for this, you can find an exact answer, because deal execution leaves evidence.

The deal’s not real unless you’ve got it in writing. So whatever your answer is after looking for the documentation, that’ll size up your execution gap. The bigger the gap, the bigger the revenue loss.

Continuing with that example: 

Writing a “good” executive summary isn’t just a single activity. It’s more of a process. It’s a combination of activities that’ll repeat across every stage. And it’ll look something like this:

After every new discovery call, your reps will have to repeat those steps to merge their new discovery in, keep their docs updated. 

Which is why it’s so rarely done. (Less than 8% of deals have one.)

Olli understands your goal, then creates and executes a sequence of tasks to get that job done:

1. Fetch the right CRM opportunity record. 
2. Process all the related email and activities. 
3. Match them up with the right transcripts in Gong / Salesloft / etc.
4. Research any major changes in public data that might impact the message.
5. Look for an existing draft, and merge your new discovery into it (vs. duplicating existing docs). 
6. OR, select the right document structure based on stage, and write a first draft.
7. Compare that new or updated draft to won/loss data, to identify the gaps.
8. Craft discovery questions to fill those gaps while sharing the draft. 
9. Write a forwardable to help your champion share the message.

That’s an example for the type of activity you already know should happen, but isn’t. 

• This can happen at a deal level: Write an executive summary for Twilio.
  
  
• Or a pipeline level: Write an exec summary for all Stage 2 deals without an executive buyer.
  
  Here, 30 - 40 clicks per deal (x) 10 deals = 300 - 400 clicks removed. To get to content that’s actually good.

Next, there’s an altogether different type of work Olli tackles with you too:

The kind that should be happening, but you don’t even think to ask about. 

Point #4: Olli suggests and proactively guides you through the right next step.

It’s way easier to keep a deal healthy than to revive a dead deal. So while you’re scrolling LinkedIn, Olli’s scrolling through every new document view, transcript, email, and change in public dataset. To match it all up with changes in deal size, stage-to-stage conversion rates, and cycle times.

It’s Olli’s favorite feed. (Yeah, he’s a nerd. But we love him for it.)

He uses those patterns to give you a gentle nudge. Or a kick in the ribs, if you ignore the nudge too many times:

Draft, discover, develop: Olli’s built-in flywheel

Eventually, Olli will have given enough reps the same nudge. Over, and over. And he’s going to get a little tired of nudging then waiting for permission from his humans. 

So eventually, he’s going to make a different type of suggestion: a playbook edit.

A specific play that Olli always has the greenlight to go ahead and execute on. Because it’s rooted in your own pipeline data:

‍Deals with the buying team’s CMO engaged by Stage 3 close 19 days faster — I’ll start drafting a forwardable email for our champions in all deals > $50k.

That’s a big deal. Because typically, this type of work gets split across 4 different job roles:

1. RevOps runs the data, finds the friction, and drives the strategy.
   
   
2. Enablement translates this into a playbook: frameworks and trainings that target the gaps.
   
   
3. Reps are then expected to execute the playbook steps by stitching together 5 - 10 tools.
   
   
4. Sales leaders are then supposed to coach reps, and reinforce the right behaviors.
   
   
5. Repeat.
   
   

For example: 

1. RevOps finds 45% of Stage 3 deals stall out. But deals moving fastest from Stage 3 → Closed Won have a buying executive engaged by Stage 2.
   
   
2. Enablement trains the team on writing executive summaries. So buyers can forward the right message to the right executive, early.
   
   
3. Reps try it out. But writing a good executive summary is hard: they find it’s less about documenting what they know. More about discovering what they don’t know.
   
   
4. Sales leaders try to coach to the above, but realize, “Holy crap, I can’t do this for 50 deals.”
   
   Then it turns out each rep’s discovery is kind of weak anyway. They don’t even have the input to write a good summary. And that’s because they didn’t start off with a solid point of view.
   
   Which is a whole other playbook step to account for in an earlier stage. (More on this soon.)

This creates a flywheel that, in most revenue orgs, only turns monthly. More often quarterly. And in some revenue orgs, only annually. Which is just too slow to build any real momentum.

But Olli turns this flywheel with you daily. 

That’s point #5: Olli writes, runs, and adapts your full sales playbook, from first call through upsell.  

Stopping deals from stalling mid-funnel is how you’ll turn the pipeline you already spent the time and cash to create into revenue. This mid-funnel focus is what’s been missing from GTM “innovation.” (All the spend for better pipeline creation just gets dumped into the same leaky bucket.)

This means Olli isn’t just for AE’s. He works across all GTM roles and stages. 

It has to be this way, too. Because revenue outcomes late-stage always flow from the right inputs early-stage:

Which brings us to our last point:

Finally, Point #6: Olli’s someone you hire, not something you “configure”

Early adopters have been building (or buying) AI agents for months now. More platforms are adding the option to add a “force” or “fleet” of up to “100 agents!” 

You can get a “deal analyzer agent.”

A "competitive threats agent.”

 A “deal summary agent.” 

A “win/loss data agent.” 

A “forecast risk agent.”

A… you get it.

Which is okay, I guess? But for most revops and enablement teams we know—the ones running on a 20:1, 30:1, or even 50:1 support ratios at times—that’s a tall ask.

How do you find the time to configure each, make them talk to each other, and then connect it all back into one cohesive GTM motion?

Shouldn’t AI be more like hiring a worker, and less like configuring a workflow?

It should feel like onboarding a colleague. Someone who:

• Brings you a point of view on how to operate.
• Gives you the benefit of their past experience and learnings.
• Learns your business, and gets better and smarter over time.

Someone you genuinely enjoy talking with. 

Which is exactly how we’d like to start. If you made it this far, I’ve got one last question for you: 

Would you like to meet Olli?

Grab a time, and we’ll introduce you two. 

Olli’s still growing up, so we’ll show you exactly where he’s at today, and you can work on your first deal together now. Then, you can decide when the time’s right to officially start working together, and watch him continue to learn over time.