Call Prep — Dan Callahan, Spectrum Reach

Thu Apr 30, 2026 · AI Training for Executive Leaders · 30-min Discovery → Close

Meeting at a glance

Date / Time

Thursday April 30, 2026 · 30 minutes

Format

Webex — join link · code 2863 402 9047

Attendees

Dan Callahan (host), Steven, Lynne Vellucci (optional, EA)

Subject line

"Steven Goulos / Dan Callahan"

Your goal

Primary Convert Dan's "yes I'm interested" into a confirmed engagement — solo or solo + Jason Brown. Secondary Open the door to a wider exec cohort across Spectrum Reach senior team.

The opening (anchor here)

This call exists because of one specific Dan reply on April 6:

"The team really enjoyed your session on AI. Yes, I would be very interested in doing this. I feel like I am getting better but would love to truly put the AI tools to work in a more proactive fashion."

That last sentence is the whole thesis of the meeting. He doesn't need to be sold on AI — he needs to be sold on himself becoming a power user. Anchor your open there: "The line that stuck with me from your reply was 'put the AI tools to work in a more proactive fashion.' That's exactly what this program is built for. Tell me what 'proactive' would look like in your week if it were working."

Account snapshot

Account	Charter Communications / Spectrum Reach (advertising sales arm, ~$1.5B annual ad revenue, top-30 US ad seller)
Status	Active relationship. Existing training delivery (CTV 101 May 2025, Intro to AI in Advertising April 1, 2026 — 700+ Charter/Spectrum sign-ups internally).
Their AI posture	Already shipping AI products to their advertisers (Spectrum Reach Architect AI media-planning platform launched 2025; Waymark partnership for AI-generated TV creative). Internal AI fluency is now a strategic priority — and lags the product.
Key champions	Dan Callahan (this call), Jeffrey Johnson (VP Learning Solutions, your operational partner), Jason Brown (EVP, Dan's boss — "JB" in your pitch).
Recent activity	Apr 1 webinar (700+ signups, push driven by Dan); Jordan Ramirez pursuing "The Power AI Seller" through her leadership chain; SarahJane Nuttall asked for the recording.

Who you're meeting with

Dan Callahan — SVP & Chief Revenue Officer, Spectrum Reach

Promoted June 2025 from Group VP, National Advertising Sales (joined 2023). Reports to / partners with EVP Jason Brown.
Background: ~10 years at Fox Networks Group; last role SVP Data Strategy & Sales Innovation — built cross-screen, audience-based sales strategies. Earlier: Director of Programmatic Sales at Fox News Digital. Wake Forest grad.
Read on him from your threads: Warm, responsive, decisive. Replies in 1–2 lines. Comfortable saying "yes" without committee. Uses Outlook for iOS — likely mobile-heavy. Has an EA (Lynne) for everything calendar-related.
What he cares about: Data strategy, sales innovation, programmatic. He came up through "make the data sing for the seller." That's also what he wants AI to do for him personally.
Personal hook open to you: You already swapped a side-conversation about your kids' summer internships at Spectrum (he said "yes we are hiring, send resumes"). Friendly, current, useful.
LinkedIn: linkedin.com/in/dan-callahan-28956015

What Dan has already seen from you (his reference points)

When	What	Why it matters here
Feb 2025	You flagged you were training Michelle Aragon's marketing team + Mac Cayton + Sean Costello.	Established credibility inside Spectrum Reach before he was CRO.
May 2025	Private CTV 101 session for ~62 Spectrum Reach attendees on 5/14.	Proved you can run a tailored private session, not just a public webinar.
Oct 2025	You asked Dan for senior-leader referrals (Jay's replacement). He responded same day with "have a few in mind, here's my cell."	Relationship is personal, not transactional.
Apr 1, 2026	Intro to AI in Advertising webinar. 700+ Charter/Spectrum sign-ups (Dan personally pushed it internally).	His own line: "appreciate the outreach… looking forward to learning with you." He's a believer. He's also a beneficiary — he saw the engagement.
Mar 26 / Apr 6 2026	You sent the exec-AI one-pager. He replied: "Yes, I would be very interested in doing this."	This call is the natural next step. Don't re-pitch — shape.

The offer he's already seen

From your March 26 email — keep this language ready in case he wants a recap:

"Four 60-minute sessions that build on each other. Starts with how to actually prompt AI to get useful output, then moves into real executive applications like board memos, competitive analysis, and strategic decision-making. The later sessions focus on building multi-step workflows and setting up a personal AI system executives can use every day."

You explicitly offered solo OR with JB (Jason Brown). That binary is still live and is the most important question of this call.

Suggested 30-minute agenda

30 minutes is tight. You only have time for one real discovery beat and one decision. Don't try to walk the four sessions slide-by-slide — get him talking about his week, then collapse straight to format + next step. Goal isn't to teach the program; it's to get a "yes, send the proposal."

Time	Block	What you're after
0–3	Open + anchor	Thank him for the April 1 push (700+ signups). Anchor on his own line: "more proactive." Set frame: "I've got 30 minutes — I want to leave with a shape we both like."
3–13	Discovery (one beat, deep)	"What does 'more proactive with AI' look like for you in a normal week?" Push for one concrete recurring task — board prep, pipeline review, strategy memo. Don't move on until you have it.
13–20	Map the program (light touch)	Don't walk all four sessions. Pick the 1–2 that map directly to what he just said. ("Session 2 is exactly that board memo problem.") Mention the four-session arc; don't dwell.
20–26	Format decision	Force the choice: solo, solo + JB, or small exec cohort (5–8). Get a leaning today even if not final. Ask: "If this works for you, who are the next 3 names?"
26–30	Close on a deliverable	"I'll send a one-page proposal by [Friday] with two options — you solo, and you + JB. Reply with the one you want and we'll book Session 1." Loop in Jeff Johnson on procurement after he picks.

Discovery questions (pick 4–5)

Since the April 1 session, has anything changed about how you personally use AI day-to-day? — Calibrates where he actually is.
When you said "more proactive" — what does that look like in a week where it's working? — Pulls the goal out in his words.
What's a recurring task — a board prep, a strategy memo, a pipeline review — where you'd want AI doing 60% of the lift? — Surfaces the use case that justifies the spend.
Is JB asking for the same thing, or is he in a different place? — Tests the solo-vs-paired path. Also flushes out whether Jason is a champion or a gatekeeper.
If this works for you, who are the next 5 people on your team who should go through it? — Plants the expansion seed before you've even started.
How does Spectrum Reach Architect change what your sellers — and you — should be doing differently? — Shows you've done your homework; bridges their AI product to his AI fluency.
What's gotten in the way the last two times you tried to make AI a daily habit? — Surfaces objections before they become objections.

Anticipated objections & responses

Likely objection	How to handle
"Four hours is a lot — can we compress?"	Yes, but the value is the spacing. Each session has homework that gets debriefed in the next. Offer 4×60 over 4–6 weeks, not 4×60 in one day. Frame: "It's a habit-build, not a tutorial."
"Let me loop in Jeff Johnson on procurement / budget."	Welcome it — Jeff already knows you and trusts you. Offer: "Happy to send the SOW to you and Jeff together so it doesn't sit." Move it forward today.
"Should we just do this for the whole team instead?"	Don't reflexively scale up. Exec power-user is a different program than seller enablement. Offer: "Let's do this with you (and JB) first — it'll inform a different curriculum for the team. Power AI Seller is the team version."
"What's different from the April 1 webinar?"	That was awareness for many. This is fluency for you. Different mode, different output. He'll be doing real work in the sessions, not watching slides.
"Can we wait till after [upfronts / Q3 / etc.]?"	Push gently: "The fastest ROI is using AI to survive the busy season, not after it. Want to start with one session before [upfront date] and finish after?"
Pricing pushback	Anchor on outcomes: hours saved per week × his calendar value. If he balks, offer the solo+JB tier as the value option (split the cost across two execs, same delivery).

Things to keep handy

Bridge to their AI products

Spectrum Reach already has Architect (AI media planning, used by 2,000+ local advertisers in trial) and the Waymark partnership (AI-generated TV spots). Their customers are getting AI tools faster than their execs are getting AI fluency. That's the gap your program closes — and it's worth saying out loud.

What "good" looks like by end of call

✅ Format committed: Solo, solo + JB, or small exec cohort.
✅ Cadence committed: Weekly or bi-weekly, start week named.
✅ Next step is a deliverable, not another meeting: "I'll send the proposal by [day]."
✅ One name beyond Dan: Either JB confirmed in or one other senior leader who should be in cohort 2.
🟡 Stretch: Tentative date for Session 1 on the calendar before you hang up.

Sources: Gmail thread "AI Training for Executive Leaders" (Mar 26 – Apr 8, 2026); calendar event "Steven Goulos /Dan Callahan" 4/30/26 11:30 AM ET; prior Spectrum Reach training threads (CTV 101 May 2025, Intro to AI in Advertising Apr 2026); public reporting on Dan Callahan's June 2025 SVP/CRO promotion (TV Tech, Adweek, Light Reading); Spectrum Reach Architect & Waymark partnership announcements.