Phil HowardEnterprise Sales
Bringing 15+ years of enterprise technology sales to AI adoption

Customers ask for what they know.
Progress starts with
what they haven't seen yet.

Every major technology shift raises the same business questions. AI is making them more urgent.

I'm Phil Howard. I spent 15+ years in B2B and enterprise sales at Verizon, then seven years leading an organization from the buyer's side of the table. Each engagement below began with a narrower request and expanded as better questions brought the larger business problem into view.

See what that looks like Email me
2003 to 2018 Verizon National Account Manager,
then Senior Client Partner Then Executive Director
O'Dwyer Retreat Center, 2018 to 2025
Phil Howard
$10M+ Annual enterprise portfolio
Senior Client Partner, Verizon

Three engagements. The numbers came after the questions.

THE ASK THE OPPORTUNITY
A global biopharmaceutical company

The ask was a discount. The opportunity was to make the refresh secure and connected.

They wanted volume pricing on a bulk mobile-hotspot order. Asking how they planned to use the devices surfaced a company-wide laptop refresh with Dell and no unified mobile-security approach. The Dell model they had specified could be custom built with an embedded mobile broadband chip, an option they had not ordered. They changed the order and paid the difference, and two devices per user became one.

See how the engagement came together
$1.6MEnterprise solution value
1,500+ mobile broadband-enabled devices
An enterprise software company that had grown by acquisition

The conversation kept returning to price. The larger problem was fragmentation.

Every conversation with the SVP of IT came back to cost. He could see 25 lines for his own team, but acquisitions had left roughly 2,000 spread across carriers, contracts, and policies. Consolidated pricing and a cost-center model preserved local accountability while creating enterprise visibility, and produced one exclusive agreement covering roughly 2,000 lines, about 1,500 of them consolidated from other carriers.

$2MEnterprise solution value
25 visible lines. 2,000 across the enterprise.
A national news and publishing organization

The headquarters agreement was the foothold.
The affiliates were the growth.

The first national agreement covered headquarters. I used it to reach the organization's 130+ affiliates, each of which made its own buying decision. As adoption grew, successive agreements carried stronger volume pricing, giving every new affiliate a clearer reason to join.

$4M+Annual service revenue
100 lines grown to 5,000+

Customers are described generically by design. I don't publish client names.

Both sides of the table

For seven years, I was the one being convinced.

I spent 15+ years making the case across financial, operational, and technical priorities. Then I spent seven years owning the consequences of all three.

15+ Years in B2B and enterprise sales

Across Fortune 500, regulated, and nationally distributed accounts: multi-year negotiations, competitive takeaways, and partner ecosystems assembled around complex customer problems.

7 Years owning the decisions

As Executive Director of a $1.5M organization serving 6,000+ people a year, I owned the P&L, operations, vendor decisions, and every capital investment. People served grew 42% over five years, and revenue grew more than 20% in one year.

A solution has to fit the people who fund it, own it, support it, and use it.

Two perspectives.
I have worked from both.

How it comes together

A single request can touch finance, operations, technology, users, and implementation. See the method I use to bring those outcomes together.

The seller's chair
What seven years on the other side taught me

Owning the budget, the tradeoffs, and the consequences changed how I evaluate every sale.

The buyer's chair
AI adoption

AI is new. The questions are not.

I spent 15+ years helping enterprises work through these questions when wireless was the emerging technology, then seven years as an executive director deciding which systems a small team could actually absorb. In both chairs the constraint was rarely ambition. It was capacity. Interest in AI is high and expectations are rising, but the harder questions are organizational.

How does a pilot become part of everyday work?

Who owns it after launch, using the team already in place?

What rules govern its use, and who is accountable for them?

The technology changes. The responsibility to make it work across the organization does not.

See AI + Judgment

How this was built

I built this site with AI, and I governed it like a deployment.

Each model brought different strengths, and their recommendations sometimes conflicted. Every one of them was fluent, confident, and occasionally wrong in ways that would have cost me credibility, not the model. So one master document became the source of truth: facts were corrected there before they moved anywhere else, customer identities stayed separate from public stories, and potential outcomes were never presented as booked results. I checked the facts, controlled the scope, challenged what came back, and made every final decision. What is published here is mine.

ClaudeDesign direction, site code, and substantial drafting.
ChatGPTStory development, fact discipline, and graphics.
GeminiIndependent second opinions on wording and diagrams.
NapkinEarly visual exploration. No final asset survived.
CloudflareHosted on Cloudflare Pages.
What I chose not to ship

Building with AI also meant deciding what did not belong in the final product.

Interview agentI built an agent that answered questions from my career story bank. One adversarial prompt produced an answer I would never have given, so I took it down rather than patch a single response.
Backend workerI built a backend service to run the site's AI features. An audit showed a protection I had relied on was not providing the control I thought it was, so I decommissioned it rather than leave an unnecessary service running.
AI BoardroomI built a working experience that brought two separate LLMs into the same conversation to debate a business question. I kept it private because open-ended public inputs could generate unreviewed outputs I could not reliably monitor or stand behind.
Open to senior enterprise sales roles

If this is the kind of enterprise selling you value,I'd like to talk.

I'm focused on senior enterprise sales roles in AI and enterprise technology where the product is worth believing in, the customer problem is complex, and judgment matters as much as activity. If that describes what you are building, a direct note is the fastest way to reach me.

What I'm looking for

A product that creates meaningful new capacity or capability for customers.

A sales organization where experienced sellers are expected to make the whole team better.

A company that listens to the people closest to the customer.

[email protected] Download Résumé LinkedIn

A direct note gets a direct answer.