30 / 60 / 90 — VP, Strategic Sales

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01 · 30 / 60 / 90 — VP, Strategic Sales

Orient → Align & Build → Activate

90 days isn't enough to solve the world's problems. It is enough to understand it, earn credibility, build the right relationships, get on deals, and deliver a plan grounded in reality — not assumptions.

Phase 1 · Orient (0–30)

I understand before I act, learning and listening

Phase 2 · Align & Build (31–60)

Segment and Organize the market, understand the team

Phase 3 · Activate (61–90)

Finalize V1 of the Strategic GTM plan with a solid idea of our ICP

Exercise

Title · 30 / 60 / 90

01 · 30 / 60 / 90 — VP, Strategic Sales

Orient → Align & Build → Activate

Phase 1 · Orient (0–30)

I understand before I act, learning and listening

Phase 2 · Align & Build (31–60)

Segment and Organize the market, understand the team

Phase 3 · Activate (61–90)

Finalize V1 of the Strategic GTM plan with a solid idea of our ICP

02 · Phase 1 · Days 0–30

Orient — I Understand Before I Act

Internal — Get Inside the Business

Structured 1:1s, every stakeholder—AEs, SEs, SDRs, RevOps, CS, Marketing, Product, Chris, Abe — structured listening: what's working, what's broken, what they need from this seat that they're not getting. Notes taken, follow-ups owned

Product ramp — hands on—certify myself on the stack: run the voice-agent demo, build with the API (already started — aivoicedemo.app), sit with SEs on POC mechanics. I can't coach a motion I can't run

Tech stack & data flow—CRM, conversation intelligence, forecasting, sequencing — where are the blind spots; I can't coach what I can't see

Pipeline & forecast audit—velocity, stage conversion, forecast accuracy, win/loss by vertical — my own view, separate from the status deck

Outside — Hear It From the Market

Customer listening calls—a cross-section of enterprise customers: why they chose us, what they're building, what would make them expand — or leave. Customer voice beats any internal narrative

Win/loss patterns—what we win and lose and why — consistent or random? Pattern recognition shapes the methodology: what to lead with, where competitors gain ground

Call film — as much as possible—recent discovery, demo, competitive calls: where AEs lose deals, where objections go unhandled, where the message lands and where it falls flat

My own competitive POV—I bring conversational-AI market context; now test Deepgram's positioning against it — talk to AEs about real competitive deals, not just the battlecards

Field — See the Motion Live

On active deals—with AEs on live opportunities — not running the deal: watching, listening, supporting. Fastest way to understand how the team sells is to see it in real time

Partner reality-check—hyperscalers, CCaaS, GSIs: what pipeline is actually generated vs a logo on a partner page — there's almost always a gap between agreement and activation

Quick wins — not forced—a stalled deal, an activatable partner thread, a customer ready to expand: I want to know

Account intel starts—AI research pipeline begins enriching the accounts list whitespace in the background — ready for tiering in week 4

03 · Day 30 – 60

Assess & Segment — the Book and the Whitespace

Three buckets. Mine the first two for the pattern; point the pattern — plus AI — at the third.

Bucket 1 · Existing Customers

Room to grow — mapped per account—more volume into the commit, new products (TTS, voice agents, audio intelligence), new use cases and business units beyond the original land

Renewal risk flagged—usage trending into or under the commit? Single-threaded relationships? CS signal pulled in early

Expansion targets set—per-account whitespace model: what they bought vs what they could run

Bucket 2 · Active Opportunities

Same lens, live deals—full potential beyond current scope — is a transcription deal actually an IVR-replacement deal in disguise?

Deal health audit—MEDDPICC gaps, multi-threading, real next steps — my own read, separate from the status deck

Shape the close plan—mutual action plans on every qualified opp; my direct involvement where the size warrants it

→ Mine the Pattern (ICP v1)

What do wins share?—vertical, use case, incumbent being displaced, deal trigger (contract expiry, AI mandate), routing stack, cloud posture

Where do leads come from?—partner-sourced vs inbound vs outbound — what actually converts, not what we assume

Output—an evidence-based ICP: where the product fits and why we win

Bucket 3 · Cold Accounts — Prioritized by the Pattern, Attacked in Order

Score it—apply ICP v1 + AI research + intent signaling + whatever GTM tooling we have (enrichment, technographics, contract-expiry signals) to rank the F500 cold list — continuously refreshed, not a one-time spreadsheet

Organize it—group where the data says to — likely regionally, then vertically (FSI, Healthcare, Telecom first, where my network also lives) — so messaging, references, and POVs compound instead of resetting per account

Assign it—handed to the team in an organized fashion: named targets per AE matched to capacity and ramp, SDR sequences built per vertical from the research — everyone knows exactly who they're attacking and why

04 · Phase 2 · Days 31–60

Align & Build — the Bench and the Motion

Team Development — Coach Through the Work

Weekly deal-review cadence—coaching through deals, not inspecting them — the AE brings the deal, I ask the questions; the quality of the questions improves the team over time

The A-player — amplify—understand where I can help, learn what works, fill in the gaps, and figure out what he needs

The new AE — ramp with gates—demo certification → shadowing → solo discovery with me in the room → weekly gates visible to both of us, role plays etc

Direct development talks—honest coaching conversations — not performance reviews — about where each AE grows; individual development plans drafted by day 60

What the team needs—by day 60 I'll have a documented view of tooling, process, capacity, and skill gaps, prioritized with Chris and RevOps: some are quick fixes

05 · Day 1 - 90

Executive Engagement — Top 10 Strategic Accounts

C-suite access is earned three ways: relationships you bring, partners who open doors, and a point of view worth the hour.

Door 1 · My Network

15+ years selling conversational AI and CCaaS to F500 C-suites in FSI, Healthcare, and Telecom — warm paths into the exact verticals this account list lives in. Week 1: map my contacts against the top 10. Warm intros beat cold exec outreach.

Target: named exec path for every top-10 account by day 45.

Door 2 · Partner Air Cover

AWS account teams hold exec relationships at every top-tier bank — co-sell explicitly includes joint executive engagement with CIOs and CCOs. Customer on Azure or GCP? Same play, different hyperscaler. CCaaS alliance execs open CX-leadership doors.

Target: AWS-sponsored exec touch in ≥3 of top 10 by day 75.

Door 3 · A POV Worth the Hour

Execs take meetings about their agenda, not our product. Per account: POV connecting their public AI commitments to a voice roadmap with containment and cost math. Deepgram exec sponsors paired per account with standing strategic account reviews.

Target: CCO / CIO meetings held in ≥5 of top 10 by day 90.

A combination of networks, partnerships, and AI research based outreach, is the key to Exec Engagement

06 · Day 1 - 90

Co-Sell — Built With the Partner Org, Not Around It

Hyperscalers — AWS First

Day 1–30—named PDM relationships; every EDP account in the book mapped; activation reality-check vs the partner page

Day 31–60—2 joint account plans with AWS FSI sellers; joint SA architecture session in every technical eval

Day 60 - 90—Ongoing account mapping, understanding accounts with EDP burn down

UCaaS / CCaaS Platforms

Day 1 – 30—Understand what Abe is looking for out of these, share my thoughts, spend a lot of time together figuring out where I can help

The play—Leverage my network — my two references other than my former boss: one runs the entire CCaaS practice at RingCentral, the other does the same at Zoom, and many similar stories.

GSIs — Delivery Scale

Why they matter—F500 IVR migrations are delivery-heavy; a GSI on the bid answers “who implements this” before procurement asks

The play—enable 1–2 GSI practices on the voice-agent stack; attach as migration partner on Tier-1 pursuits

This is probably the most important part of the plan, life in the F500 list goes a lot easier with partners, I have extensive knowledge of the ecosystem, huge network of relationships

We are 3 hour drive apart, my goal after 90 days would be to have a locked down GTM plan for the Strategic Accounts team as it relates to partners, as well as where I can help, with my network and background in partnerships, anything you aren't currently doing or may not have thought of.

08 · Phase 3 · Days 61–90

Activate — Deliverables and the First 3 KPIs

I look for early stage, leading indicators for success, I've rarely had a problem closing deals, or making them larger

First 3 KPIs – Sales / Reps

1 · Qualified pipeline created—new qualified opps + discovery meetings vs ramp-adjusted weekly targets — the input that predicts everything

2 · Active POCs—How many active POCs are in flight, their status, typical closure rates and next steps

3 · Multi-thread & co-sell attach—VP+ contacts per opp, % partner-attached — single-threaded deals die; partner-attached deals close bigger, faster

My 90-Day Scorecard

1 · Product Knowledge—Deep understanding of our tech stack

2 · Internal Stakeholders—Understand who to go to, and for what, have relationships with key players in the internal team

3 · Understanding the current sales “situation”—Pipeline, GTM motion, why we win, why we lose, forecast accuracy and cadences

Develop and present V1 of the Strategic GTM plan with a solid idea of our ICP, what the team needs, how we work with channel, hiring plan, forecast, recommend changes etc