Sales Scientist · Revenue Economist · Still In The Field

Your reps know
the playbook.
They stopped
believing it.

You've built the team. You've bought the tools. The pipeline hasn't followed. That gap, between a team that knows what to do and a team that believes it will work, is the most expensive problem in high-growth SaaS. And it's the one problem most SKOs aren't designed to fix.

Book the Keynote Who is this?
Gerry Hill — Sales Scientist, Revenue Economist, SKO Keynote Speaker

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Who Is This

Most speakers have one
data point: their career.
Gerry has tens of thousands.

Most sales authorities have one data point: their own career. A CRO who scaled one company. A consultant who built one playbook. One data point is a story. Gerry Hill has tens of thousands.

Over 20 years as an operator, a market-builder, a CRO, and the person responsible for revenue intelligence across some of the highest-volume outbound platforms in the world, he has spent time inside the numbers of tens of thousands of companies trying to grow their market share. He has seen what baseline looks like. He has seen what winning looks like. He knows what separates them. Not from a sample or a study. From having seen both ends of it thousands of times.

At ConnectAndSell, he operated inside the world's highest-velocity outbound infrastructure for six years, observing connect rates, conversation frequency, and pipeline velocity across hundreds of outbound revenue motions; founder-led, SDR-led, AE-led, and hybrid. In real time, not reconstructed from reports. Today he works daily across hundreds of live accounts, seeing data most organisations have never looked at and most consultants have never been near.

That is a different kind of knowledge to anything a single career produces. A practitioner knows what worked for them. Gerry knows what works across the distribution: what the bottom quartile does, what the top quartile does differently, and exactly which variable, changed, moves a company from one to the other.

That variable is almost never the one the organisation thinks it is. And it shows up most clearly, and is most fixable, in high-growth companies between Series B and Series D, where the outbound motion is scaling faster than the conviction that powers it.

The Point of View

Pipeline culture didn't erode overnight. Here's the exact timeline.

This isn't a historical thesis. It's what he sees every week, in live accounts, in real conversations, right now. The pattern hasn't changed. The cost of ignoring it has.

Pre-2003
Pipeline was a shared organisational effort. Senior people opened doors. Relationships created conversations. Individual sellers were not left alone to generate everything from scratch.
2003 – 2012
The industrialisation of Predictable Revenue. Pipeline became a factory. SDRs replaced relationships. Volume replaced skill. The model promised repeatability and delivered it — at the cost of the craft.
2012 – 2022
Automation finished the job. Sequences, cadences, AI-generated personalisation. Conviction became optional. Why develop the skill to have a hard conversation when a tool could send fifty emails before breakfast? It killed the muscle entirely.
Now
The second wave is crashing. The age of efficiency demands every conversation is earned. And for high-growth companies specifically, there is a second crisis: the founder who used to make the calls has stopped, and the team hired to replace them has inherited the tools but not the conviction.
850–1,200%
The conversion improvement on circle backs versus cold outreach when reps execute on them. Observed across live outbound environments over 20 years, across multiple verticals and deal sizes. Most teams have these opportunities sitting in their stack right now. The reason they are not being worked is not a process problem. It is a conviction problem. That is what every PipelineOS session is built to fix.
Core Belief 01
Tactical execution drives strategic outcomes. Not the other way round. Reps act their way into believing.
Core Belief 02
The phone isn't dead. Your team's relationship with rejection is. Fix that, and you fix the pipeline.
Core Belief 03
Market dominance happens when you activate conversations at scale. Not when you add another sequencer.
Core Belief 04
Coach the aggregated data, not the individual seller. Kill glitchy first-line coaching behaviours overnight.
Core Belief 05
An SKO that doesn't change behaviour is a party. Your CRO isn't paying for parties.
What I Have Seen

I've been inside the outbound operations of tens of thousands of companies. Founder-led, SDR-led, AE-led. Pre-revenue to post-IPO. Every vertical, every deal size, every structure.

What that produces is not a point of view. It is a distribution. I know what the bottom of the market does. I know what winning looks like. And I know, with a clarity that someone who's only ever run one team simply can't have, exactly which variable, changed, moves a team from one to the other.

That variable is almost never the one the organisation thinks it is. It is not the sequence. It is not the messaging. It is not the tool. It is the belief, inside each rep, that the next conversation is worth initiating. Every SKO I deliver is built around restoring that belief, with the data to back it up.

And because I am still in the field every day, working across live outbound motions, not describing ones I left behind. The benchmarks in your session are current. What's working this week is what gets built into your SKO.

What CROs Say

The only proof that counts.

"Gerry doesn't run an SKO session. He runs a diagnostic with a room full of people. He identified the exact belief gap in our outbound motion inside the first twenty minutes. The rest of the day was spent systematically dismantling it. Connect rates moved in week three. Our managers are still using the inspection language six months later."

VP Revenue
Series B SaaS · 60-person sales team · UK

"I've sat through a lot of outbound keynotes. Most of them are the same recycled tips dressed up with new slides. Gerry came in with our own pipeline data, our own connect rate benchmarks, and a framework that made the whole room uncomfortable in the best possible way. Three of my AEs told me it was the first time they'd understood why they weren't hitting number. That's not inspiration. That's surgery."

CRO
Enterprise SaaS · PE-backed · North America

"What separates Gerry from every other facilitator I've hired is that he's still operating. He's not describing a world from five years ago. He's working across live accounts every week. When he quotes a connect rate benchmark, it's not from a report. That credibility is felt in the room. Reps don't argue with it. They write it down."

Head of Revenue Enablement
High-growth SaaS · HubSpot ecosystem · EMEA

"We brought Gerry in to get our outbound team back on the phone. We'd tried two other enablement programmes. Neither moved the number. His workshop produced a measurable shift in outbound activity within the first fortnight, and the shift held. The framework gave our managers something concrete to inspect against, which is what every other programme had been missing."

CCO
Scale-up SaaS · Series C · London
Formats

One thesis. Three formats. Zero filler.

🎤
Single Session

The Pipeline Conviction Address

45–60 minutes. Built for teams at an inflection point: enough people to have lost the founder-led conviction and not yet enough structure to have replaced it. Reframes how your entire revenue team thinks about pipeline. Bespoke to your data and stage.

  • Pre-event diagnostic call with CRO or VP Sales
  • Deck built around your pipeline ratios and product
  • Live outbound demonstration: real calls, real accounts, in the room
  • Post-event manager resource pack
What you leave with
A shared diagnostic: the specific belief gap in your team, named, and a single, clear next action every rep has committed to before leaving the room.
⚙️
Most Requested

PipelineOS Workshop

The format built for high-growth teams of 10–60. Not a talk. A working session that installs the PipelineOS framework directly into your team. Reps leave with a functioning pipeline architecture. Managers leave with the language to inspect it.

  • Full day, 10–40 participants (cohorts for larger teams)
  • Live outbound & phone practice blocks
  • Individual pipeline architecture on paper, completed in the room
  • Manager inspection guide (what to ask, when, and why)
  • 30-day check-in structure: three manager-led reviews with specific prompts
What you leave with
Every rep holds a completed, personalised pipeline architecture document. Every manager receives a printed 30-day Manager Inspection Guide: a standalone tool with specific coaching prompts for weeks 1, 2, and 4, designed to be used in 1:1s without any further input from Gerry.
🏗️
Embedded

SKO Programme Architecture

For Series C and beyond, when your SKO has multiple tracks, internal presenters, and a management layer that needs its own framework. One thesis running through the whole event. Every session designed to compound, not compete.

  • Full SKO agenda design and narrative architecture
  • Briefing and preparation for internal presenters
  • Manager track: parallel or sequential
  • Keynote + workshop delivery included
  • 90-day CRO accountability calls: monthly, 30 minutes, on the numbers
What you leave with
A complete SKO narrative, a manager toolkit, and a 90-day operating cadence, so the investment doesn't evaporate in week two.
The Framework

PipelineOS: the operating system for outbound revenue.

Pipeline Heroes is the practice. PipelineOS is the framework it delivers. A set of principles that work together, each one connected to the next, turning pipeline creation from something you're born with into something you can actually build. Built from 20 years operating inside the highest-performing outbound teams in B2B SaaS.

Proven across high-growth revenue teams. Every SKO session anchors to at least two pillars. Every workshop installs the whole framework. PipelineOS is currently being written as a full-length book for publication. Clients who engage now help shape the final manuscript.

01
The Conviction Engine
Belief architecture & rejection recalibration
→
02
The Physics of Pipeline
Activity ratios, connect rates & system inputs
→
03
Call Timing Logic
When, who & how to call for maximum connect rate
→
04
The Sequencer Trap
Why automation killed conviction & how to restore it
→
05
The Narrative Close
Storytelling as a pipeline instrument
→
06
Pipeline Ownership Architecture
AEs own their number, without depending on SDRs
→
North Star Metric
Conversations Per Day
Not dials. Not tasks. Not touchpoints. The only number that predicts pipeline. Meaningful conversations initiated each working day.
Input
Intent Signal
Who to call, ranked by propensity to answer and buy.
Execution
Conviction + Cadence
The belief to dial, the skill to navigate, the rhythm to sustain it.
Outcome
Self-Sourced Pipeline
Revenue that doesn't depend on Marketing, SDRs, or inbound luck.
Reinforcement
Manager OS
Coaching language and inspection cadences that outlast the SKO room.
Why Different

Not another motivational Tuesday.

DimensionTypical SKO SpeakerGerry Hill / PipelineOS
Origin✗Author or consultant with one great story✓Has observed the full performance distribution. 10,000+ companies' outbound efforts, from the ones that struggle to the ones that win. Not one playbook. The whole range.
Currency✗Describing what worked when they last ran a team, often years ago✓Still in the field daily, working across hundreds of live accounts on connect rate and prospecting excellence every week
Data✗Industry surveys and anecdotes✓Production connect rates, how fast reps are having conversations, and cost-per-conversation models from hundreds of live outbound teams across every function and structure, tracked over time
Content✗Generic framework adapted during sound-check✓Pre-event diagnostic, bespoke deck, your pipeline ratios. Not slide 14 from last month.
The Phone✗Politely avoided✓The entire thesis. Live dialling. Real calls. The arithmetic of 850–1,200% improvement explained and demonstrated.
Takeaway✗Inspirational quotes and a PDF nobody reads✓A completed, personalised pipeline architecture document. Every rep, in the room, on the day.
Stage fit✗Built for enterprise complexity, oversized for a 20-person team burning cash✓Designed specifically for high-growth teams at Series B–D, where the founder stopped making the calls and nobody else has picked it up yet
Post-SKO✗LinkedIn post and invoice✓Manager inspection guide, 30-day review structure with specific prompts, 90-day CRO accountability calls

"Market dominance happens when you activate conversations at scale. Not when you add another sequencer."

How It Works

Brief to behavioural change.

01
Diagnostic Call

30 minutes with your CRO or VP Sales. We map your pipeline health, where your team has lost confidence, and what you actually want the SKO to change. No prep required. Just an honest conversation about where the revenue problem actually lives.

Turnaround: 48hrs to proposal
02
Bespoke Build

PipelineOS rebuilt around your product, ICP, pipeline data, and team language. Your reps hear their world, not a playbook they mentally opt out of by slide three.

Typical lead time: 3–4 weeks
03
Delivery

Heavy on data, high on energy, built for behaviour change. Not applause. Live phone demonstrations, real data, and a room that leaves with something written down, a working pipeline architecture, not just good intentions.

Half day, full day, or multi-day
04
Reinforcement

Manager inspection guide, week-1/2/4 review prompts, and 90-day CRO accountability calls. The bit that stops the whole thing evaporating by the following Monday.

Included in all formats
Key Concepts

Defined terms. Precisely.

The language of PipelineOS is specific. These definitions are the foundation of every session.

Frequently Asked

Questions CROs ask before they book.

How is this different from standard sales training?

Standard sales training installs skills. PipelineOS installs belief. Skills without conviction produce reps who know what to do and still don't do it. The primary intervention in every PipelineOS session is conviction: rebuilding the case, from the inside out, for why picking up the phone is worth it. Skills follow conviction. Not the other way around.

How do you measure whether the SKO worked?

Three metrics in the 30 days after the event: conversation frequency per AE per day, are reps starting outbound activity without being chased, and are managers actually coaching to the same standard. If none of these moved, the SKO produced inspiration, not behaviour change. Every PipelineOS engagement includes a 30-day measurement framework so you know by day 30 whether the investment is working.

We have 120 AEs. Can you scale this?

Yes. For larger populations, the workshop is delivered in cohorts of up to 40 participants, typically structured as consecutive days or across the SKO programme. The manager track runs in parallel, so team leads are equipped to reinforce the framework before the first cohort session ends.

We've done outbound training before and it didn't hold. Why would this be different?

Most outbound training falls apart in week two, not on the day. Reps leave energised, managers don't have the language to sustain it, and by week two it's gone. PipelineOS addresses this with a manager inspection guide that gives first-line managers specific prompts for weeks 1, 2, and 4, plus a 30-day check-in structure. The framework gives managers something concrete to inspect against, which is what every failed programme was missing.

Is the content bespoke or off the shelf?

The framework is fixed. The application is bespoke. Every engagement starts with a diagnostic call to understand your pipeline numbers, your specific confidence problem, your ICP, and your product. The session your reps attend is built around that conversation. The framework does not change. The examples, the data, the language, and the diagnosis do. There is a difference between a consultant who rewrites their slides and one who builds their session around your reality. That is the distinction here.

Are you still working with live accounts or is this based on past experience?

Both, and the distinction matters. Gerry works across hundreds of live accounts on connect rate and prospecting excellence every day. The benchmarks in every PipelineOS session are drawn from current production environments, not archived case studies. When a connect rate figure is quoted in the room, it reflects what is happening in live accounts this week.

Is Pipeline Heroes connected to a software vendor?

No. Pipeline Heroes is an independent practice. The PipelineOS framework is Gerry's own methodology and has no commercial relationship with any outbound technology vendor. It works alongside whatever stack your team already uses. Gerry's background includes operating inside high-velocity outbound platforms, which is where much of the benchmark data comes from, but the practice itself sells nothing except the engagement.

Next Steps

Q1 and Q2 SKO slots.
They go early.

Gerry takes a limited number of engagements per quarter to ensure every session gets the diagnostic time it needs. If your SKO window is Q1 or Q2, the conversation needs to start now.

Book the Diagnostic Call → ↗ Request the Speaking Deck