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. It's also the only one most SKOs are not designed to fix.

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

Trusted by & worked with

Who Is This

He has seen the full
distribution. Baseline
to dominance. At scale.

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 revenue intelligence layer across some of the world's most data-rich outbound platforms — he has sat inside the performance data of tens of thousands of companies' market dominance missions. He has seen what baseline looks like. He has seen what winning looks like. He knows the precise criteria that separate them — not from a sample, from the full distribution.

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 — longitudinally, in production. Today he works daily across hundreds of live accounts, with access to the performance baselines and the criteria for market dominance that most organisations have never measured and most consultants have never seen.

The insight this produces is categorically different from practitioner experience. 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 is most acutely visible — and 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.

What follows is not a historical analysis. It is the diagnosis he arrives at every week — across cold start outbound environments and established revenue motions alike — from live accounts, live data, live conversations. The pattern is consistent. The urgency is current.

Pre-2003
Pipeline was strategic work. CXOs were involved. Conversations happened. The model was simple and it worked.
2003 – 2012
Prospects disappeared behind technology. Pipeline became tactical. Sellers became the primary unit of execution and CXOs stepped back from the frontline.
2012 – 2022
The second wave: digital advertising, instant lead forms, robotic social outreach, email automation, chatbots. It promised effortless conversations. It delivered the illusion of them.
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%
Across every growth stage — from pre-revenue to post-IPO — the variable that separates the top quartile from the rest is not message quality, persona research, or sequence design. It is conversation frequency. Teams logging one meaningful conversation every 90 minutes, and teams logging one every four minutes, operate in different economies of pipeline. The difference is 850 to 1,200 per cent. That is arithmetic, not aspiration.
Core Belief 01
Tactical execution drives strategic outcomes. Not the other way. 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 have sat inside the outbound motions of tens of thousands of companies. Founder-led. SDR-led. AE-led. Pre-revenue to post-IPO. Across 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 precision that no single-career practitioner can match — 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 prove it deserves to be restored.

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 is 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, 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 holds a 30-day inspection guide with specific prompts for weeks 1, 2, and 4.
🏗️
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. An architecture of interconnected principles that turns pipeline creation from an art into a repeatable, measurable system — 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.

01
The Conviction Engine
Belief architecture & rejection recalibration
→
02
The Physics of Pipeline
Activity ratios, connect rates & system inputs
→
03
Call Intent 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' market dominance missions, from baseline to winning criteria. Not one playbook. The complete 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, conversation velocity benchmarks, and cost-per-conversation models from hundreds of outbound revenue motions — observed longitudinally across every function and structure
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-led conviction has left and the replacement hasn't arrived
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, the specific conviction gap in your outbound motion, and your SKO objectives. 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

Evidence-dense, high-energy, built for behaviour change — not applause. Live phone demonstrations, real data, and a room that leaves with completed pipeline architectures, not aspirational 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 scaffolding that makes the investment last past the Monday morning stand-up.

Included in all formats
Key Concepts

Defined terms. Precisely.

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

What is PipelineOS?

PipelineOS is a commercial operating system for outbound revenue creation. It is structured around six pillars — The Conviction Engine, The Physics of Pipeline, Phone Intent Logic, The Sequencer Trap, The Narrative Close, and Pipeline Ownership Architecture — and uses Conversations Per Day as its North Star Metric. It is the framework delivered by Pipeline Heroes inside SKO keynotes and workshops.

What is conversation frequency?

Conversation frequency is the number of meaningful two-way conversations a sales representative initiates each working day. It is distinct from dials, tasks, and touchpoints. Observed across hundreds of outbound revenue motions — it is the single most predictive leading indicator of pipeline attainment — more predictive than message quality, persona research, or sequence design.

What is a conviction gap?

A conviction gap is the difference between what a sales representative intellectually knows — about their product, their market, their technique — and what they actually believe will happen when they initiate an outbound conversation. It is identified within PipelineOS as the primary cause of declining outbound pipeline creation in B2B SaaS, and the problem that most SKO programmes fail to address.

What is Phone Intent?

Phone Intent is a call intent signal that indicates when a B2B prospect is most likely to answer an outbound call, based on behavioural and contextual data. It ranks outbound targets by propensity to answer and propensity to buy. It forms the input layer of the PipelineOS framework and is observed in live accounts across hundreds of outbound revenue motions.

What is aggregated data coaching?

Aggregated data coaching is a sales management model in which first-line managers coach patterns observed across a team population, rather than diagnosing individual rep behaviour. It correlates skills to business outcomes at cohort level, eliminates inconsistent coaching, and produces measurable improvement in pipeline creation velocity at scale. It is one of the six pillars of PipelineOS.

What is the outbound pipeline conviction crisis?

The outbound pipeline conviction crisis refers to the structural decline in AE willingness and belief in self-sourced pipeline creation following the automation wave of 2012-2022. As sequencers, AI tools, and social automation replaced direct phone-based prospecting, a generation of sales representatives lost the belief that outbound conversation was worth initiating. The crisis is not a skills problem. It is a conviction problem — and it requires a different kind of intervention to fix.

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 don't do it. The primary intervention in every PipelineOS session is the conviction architecture — rebuilding the internal evidence base that makes a rep believe the next call is worth making. 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, outbound self-initiation rate, and manager inspection consistency. 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 fails at the reinforcement layer — not the delivery layer. Reps leave energised; managers don't have the language to sustain it; by week two it has dissipated. 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 proprietary. The content is always bespoke. Every engagement starts with a diagnostic call that extracts your pipeline ratios, your team's specific conviction gap, your ICP, and your product. The session your reps attend has your data in it — not the data from last month's client.

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.

Next Steps

Q1 and Q2 SKO slots.
They go early.

If your reps need to be back on the phone this quarter — and your SKO is the mechanism — the diagnostic call takes 30 minutes. Everything else follows from that.

Book the Diagnostic Call → ↗ Request the Speaking Deck