Phil HowardEnterprise Sales
Fifteen years of deals, on the record

The first ask is rarely
the whole opportunity.

I'm Phil Howard. Fifteen-plus years selling enterprise technology at Verizon, then seven years on the other side of the table, as the person every pitch was trying to convince. The deals below all started as a request for something smaller than what the customer actually needed.

Put me on the spot Email me

An agent trained on fifteen years of my actual deals.

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
Washington DC and the East Coast Selected work ↓
Selected work

Three deals, with the numbers attached.

Customers open with what they think they need. Every row here started somewhere smaller than where it ended, and the distance between those two points is the job.

THE ASK THE OPPORTUNITY
2014 to 2018Senior Client Partner
Verizon
An enterprise customer with a large mobile field workforce

The ask was devices. The opportunity was bigger.

A referral came in asking for a discount on a few hundred mobile hotspots. Unpacking why they wanted them surfaced the real problem: the company had no unified mobile security policy at all. I assembled Dell for hardware, IBM for systems integration, Verizon engineering for the private network, the customer's own operations team, and a national implementation team I built for the rollout.

$1.6MTwo-year contract value
1,500+ devices nationwide
2003 to 2014National Account Manager
Verizon
A national news and publishing organization

Headquarters was never the win. It was the instrument.

The first national agreement covered headquarters only. I used it to reach the organization's 130+ affiliates, each of which made its own buying decision, and engineered successive contracts with higher discount tiers as volume grew. Pricing improved as adoption spread, so every new affiliate had a stronger reason to join than the one before it.

$4M+Annual service revenue
100 lines grown to 5,000+
2014 to 2018Senior Client Partner
Verizon
An enterprise software company that had grown by acquisition

They only ever asked about price. Price was not the problem.

Every conversation with the SVP of IT came back to how cheap I could make it. They knew about the 25 lines their own team could see. The company actually had 2,000 across the business, scattered among carriers with no central policy and no governance. I built consolidated pricing with Verizon Finance, gave him visibility he had never had, and closed it as an exclusive agreement.

30%+Aggregate savings
~2,000 lines, one agreement

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.

Most sellers argue the same three lenses from one side of the table for an entire career. I spent seven years holding all three myself, with the budget in my name and no one else to hand the decision to.

15+ Years selling it

Verizon, National Account Manager and then Senior Client Partner. Fortune 500, regulated and nationally distributed accounts. Multi-year negotiation, competitive takeaways, and partner ecosystems assembled around problems the customer had not yet scoped.

7 Years on the other side

Executive Director of a $1.5M organization serving 6,000+ people a year across 125+ groups. I owned the P&L, the vendor conversations and every technology decision. Participation grew 42% over five years and revenue grew 20%+ in a single year.

The CFO

What happens if it doesn't pay for itself?

Cost, savings, revenue impact, risk and return. A CFO is not asking what the thing does. They are asking what it costs, what it returns, and what happens to them if it fails. Answer the first question well and ignore the last one, and the deal quietly stalls at final approval with no explanation.

What I ask themWhat would this need to return before signing it stops being a risk?
The COO

What happens the day it breaks?

Capacity, speed, reliability, and what happens the day something breaks. Operations does not care about the platform. They care whether the job gets faster and more dependable, whether their people can absorb the change, and whether the thing holds up in the field rather than in the demo.

What I ask themWhere is the current process costing you the most time?
The CIO

Who is still supporting this in three years?

Security, scale, and fit with everything that already exists. Technology leaders inherit the decision long after everyone else has moved on to the next thing. They are asking whether it integrates, whether it is defensible, and whether it still works at ten times the volume.

What I ask themWhat would make this impossible for your team to support?

A solution does not scale because the technology supports more users. It scales when every stakeholder can see the outcome that matters to them.

SOLUTION CIO COO CFO CISO IT BALANCES WHEN THEY ALL SEE IT
Open to senior enterprise sales roles

You have read the deals.
Now ask the questions.

I'm looking for a senior enterprise sales role in AI and technology, and I'm being deliberate rather than broad about it. If the way I work fits what you are building, a direct note is the fastest way in.

[email protected] Put me on the spot

Or interrogate the agent instead. It has the same fifteen years and no talking points.