Chapter 4 of 11

The Demo

Tuesday · 11:00 AM

The most important thirty minutes in the whole journey. Vicky frames it: ThreatCaptain isn't a cybersecurity product — it's the platform that helps Harbor Point sell more cyber.

Beat

#10Vicky runs the demo and discovery — the actual scripts

Vicky has prepared the demo sandbox with Wilmington as the geography and pediatrics as a test client vertical — Sundial Pediatrics. Critical framing: Vicky is not selling cybersecurity to Harbor Point. ThreatCaptain isn't a cybersecurity product. Vicky is selling Harbor Point a platform that helps Harbor Point sell more cybersecurity to its own clients — and helps them find better-qualified prospects to begin with.

Phase 1 · Upfront Contract & The Frame (3–4 min)

Vicky Bruns · VP of Channel Engagement

Kevin, Theo, Brent — thanks for the time. Before I show you anything, I want to be clear about why we're here. ThreatCaptain isn't a cybersecurity product. We don't sell security to your clients — Theo does that, Brent does that, and the SentinelOne / Huntress / Proofpoint stack you already buy through Pax8 does that. ThreatCaptain is a platform that helps Harbor Point sell more cybersecurity to your own clients, and helps you find better-qualified prospects to begin with. So this isn't a pitch about cyber. It's a conversation about your sales pipeline.

Vicky Bruns · VP of Channel Engagement

Here's how I'd like to use the next thirty minutes. The first five-to-ten minutes, understanding where your team is struggling — what does the security sales conversation look like when it goes well, what does it look like when it doesn't, and where in your pipeline are you losing the most deals. About fifteen minutes inside the platform, where I'll show you how it solves what we just talked about — using a real client of yours, live. Last ten minutes, we decide whether this fits and what next looks like. Either answer is fine. Sound good?

Kevin Whitaker · Founder & CEO

Sounds good.

Phase 2 · Discovery: Find the Pain Point (5–7 min)

Vicky isn't filling out a discovery sheet — she's hunting for the moment Kevin names a deal that died, and why.

Vicky Bruns · VP of Channel Engagement

Kevin, talk to me about security at Harbor Point. Where did you hope you'd be by now and where are you actually?

Kevin Whitaker · Founder & CEO

Eighteen months ago I told my board we'd be at $480K in annual recurring security revenue. We're at maybe $90K. Attach rate's still 22%.

Vicky Bruns · VP of Channel Engagement

What's it costing you to be flat?

Kevin Whitaker · Founder & CEO

Hard number? About $390K we should have. Soft number? Theo and Brent are frustrated. I'm frustrated.

Vicky Bruns · VP of Channel Engagement

Walk me through your last losing security deal. Where in the pipeline did it break?

Kevin Whitaker · Founder & CEO

Atlas Rigging. Manufacturing client, 80 employees. Three weeks ago. Theo did a beautiful technical assessment — eighteen pages, very detailed. Brent put together pricing. We sat across from the owner and three of his VPs for forty-five minutes. The owner kept asking 'OK so what does this actually mean for me' and we kept answering with the technical findings. We left, they ghosted us, and last week I heard they bought the cheapest tier from a competitor.

Vicky Bruns · VP of Channel Engagement

So the deal didn't die because the assessment was wrong. It died because the conversation never connected to the owner's language.

Kevin Whitaker · Founder & CEO

Exactly that. That's the whole pattern.

Phase 3 · Show the Platform Solving That Exact Pain (15 min)

Vicky Bruns · VP of Channel Engagement

OK. Let me show you what would have changed in the Atlas Rigging meeting. You named Sundial Pediatrics on the prep form — let's load Sundial and watch the platform translate Theo's technical work into the owner's language.

Vicky shares her screen. The platform pulls Sundial's public profile.

Vicky Bruns · VP of Channel Engagement

Twenty-three employees, about $4.2M in revenue, pediatric medical practice. Now I'm running our breach impact model. Average ransomware event in pediatric medical, twenty-three employees, takes the practice down for an average of fourteen days. Patient records exposure, assuming a HIPAA-compliant practice with average controls, runs $1.4M in regulatory fine ceiling. Lost revenue at fourteen days down: $161K. Reputational drag — patient churn modeling specific to pediatrics — adds another $290K over twenty-four months. Total expected loss for a single ransomware event at Sundial: $1.86M.

Vicky Bruns · VP of Channel Engagement

Theo — you've assessed Sundial. Is that number defensible?

Theo Pham · vCISO

Yeah. Honestly that's conservative.

Sundial baseline expected loss

$1.86M

Insurance Health Score

410 / 850

Shield %

13%

Attack success likelihood

87%

Vicky Bruns · VP of Channel Engagement

Now watch what the Risk Likelihood Simulator does. I'm going to layer in the security stack Theo would actually deploy — endpoint, email security, backup with tested restore, vCISO services, BOATS-aligned IR plan, the full Harbor Point security tier. Watch the numbers move in real time.

Vicky Bruns · VP of Channel Engagement

Endpoint and EDR — Shield jumps from 13% to 41%. Email security — 41% to 58%. Backup with tested restore — recovery time crashes from fourteen days to thirty-six hours. vCISO services and the IR plan — Shield to 95%, recovery time under twenty-four hours. Final state: expected loss drops from $1.86M to $24,000. Attack success likelihood drops from 87% to 5%. Insurance Health Score moves from 410 to 780. And we can bring that $1.86M with an 87% attack success likelihood down to $24,000 with a 5% attack success likelihood for $1,750 a month. That's the conversation Brent walks Sundial's owner through.

Brent Olszewski · Account Executive

Holy shit.

Sundial protected expected loss

$24,000

Insurance Health Score

780 / 850

Shield %

95%

Attack success likelihood

Vicky Bruns · VP of Channel Engagement

And the platform does this for every prospect — including the eleven net-new prospects in the lead identification module that fit your Wilmington pediatrics and dental ICP. So the second pain — flat lead pipeline — has the same answer.

Open item · attack-success likelihood metric

The line "87% → 5%" is the right framing, but the platform doesn't display attack-success likelihood as a single percentage today. Mathematically derivable from Shield % (87% = 100% − 13%), but should be displayed natively. Tracked for product roadmap.

Phase 4 · Decision & Pricing (5–7 min)

Vicky Bruns · VP of Channel Engagement

What I'd recommend is a 14-day Maiden Voyage — actually 10 business days, Monday to Friday, twice — a guided trial Kerry runs. You bring Sundial and two other real clients into the platform, plus a net-new prospect from the lead identification module. Two 60-minute group cohort calls with Kerry. Office hours Tuesday and Thursday both weeks. Inside the platform, our AI agent Beakon coaches Brent and Theo in real time. If you want more, Pro Services is the paid 1:1 path. Card on file. Cancel any time. If you do nothing, the annual contract auto-engages on Day 14.

Kevin Whitaker · Founder & CEO

What does it cost?

Vicky Bruns · VP of Channel Engagement

Base subscription is $1,699 a month on an annual contract. Includes your first five seats. After five seats, $25 per additional seat per month. Then a consumption fee for the AI enrichment — tokens that fuel the breach simulation, lead identification, and proposal generation. The math: one closed Sundial-sized security tier at $1,750 a month covers the base, the seats, and average consumption with room left over. Every deal after that is profit.

Theo Pham · vCISO

How do you want our data?

Vicky Bruns · VP of Channel Engagement

For the Voyage, just the public data and three real clients you load yourself. We don't need any integrations beyond HubSpot — that's the only system we go live with today.

Kevin Whitaker · Founder & CEO

Set it up.

Open item · pricing reconciliation

BOS 2.6 currently documents seat overage at $50/seat and 100 AI credits/mo included with $1/credit overage. Adam's 2026-05-04 direction sets seat overage at $25 and frames AI as a "consumption fee." These can't both be canon.

Beat

#11Vicky moves Harbor Point into the Maiden Voyage

Day 0 Kickoff: Monday May 18, 1:00 PM ET. Day 14 Outcomes: Monday June 1, 1:00 PM ET. Office hours Tue May 19, Thu May 21, Tue May 26, Thu May 28 — four 60-minute drop-in sessions with 15-minute bookable slots. Beakon coaches in-platform across all 10 business days. That is the entire human-time budget per Voyage.

Beat

#12Group cohort vs. 1:1 Pro Services

Kevin Whitaker · Founder & CEO

Do we get one-on-one help, or is this group?

Vicky Bruns · VP of Channel Engagement

Group plus the AI. Two 60-minute Monday calls with Kerry, four office-hours sessions over the two weeks, and Beakon inside the platform doing the per-deal coaching all day every day. If you want fully bespoke 1:1 work beyond that, Pro Services is the paid path. For a team your size, the cohort is the move. Beakon does more 1:1 coaching in a day than any human ever could.

Kevin Whitaker · Founder & CEO

Cohort.

Beat

#13Card on file

Vicky walks Kevin through the card collection language verbatim from the 2.1 Phase 5 talk track. Kevin puts the company Amex in. Theo — who hates sales precisely because he's watched too many sales calls feel like manipulation — visibly relaxes. He'd been bracing for the slick pivot, the artificial urgency, the "sign today" close. Vicky just collected the card the way you'd collect a deposit at a hotel — no theater, no pressure, cancel any time in two weeks.

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