Jim McHugh — Enterprise Account Executive · Digitally Native Businesses

About

Where I play.

Enterprise Account Executive covering AMER Northeast. My segment is digitally native businesses — AI-native startups, modern SaaS, the buyers shipping the next layer of software. Average deal $300K–$500K. Cycles 6–9 months. Outcome: customers who renew bigger.

What's changed about enterprise sales: the modern AI-native company doesn't sell to one buyer. Engineering picks the platform, but sales, marketing, finance, HR, and IT all become users in the first year — and all of them have a vote at renewal. I built the technical fluency to handle the first conversation, and the executive credibility to handle the last one. The rest is repetition.

How I Sell

What you're hiring.

C-suite

Selling business outcomes, not features

I lead with the value — TCO reduction, engineering capacity freed, time-to-revenue, governance risk retired. The dollar figure is the proof. ROI conversations with a CEO, CFO, CIO, or CAIO are where I close.

Cross-functional

Selling across the business — the modern AI buyer

AI-native companies don't sell to IT — they sell to every function. Engineering buys the platform. Sales runs the agents. Marketing analyzes the signal. Finance defends the spend. HR drives adoption. IT governs it all. I've carried those conversations in the same account.

Engineering Sales Marketing Finance HR IT

10+

Net-new logos in competitive accounts

#1 in net-new logos company-wide for two consecutive years. I build pipeline from cold — outbound, ABM, partnerships, events — and convert it. Greenfield doesn't scare me; I built Couchbase's East region from zero.

$3M

Land-and-expand at seven-figure scale

MEDDPICC, multi-threaded, patient. Closed a $1.2M ACV deal across 10+ stakeholders in 12 months — then converted a renewal into a $3M TCV multi-year expansion. 60%+ POC win rate.

Hands-on

Technical credibility without the credential

Vector search, RAG, MCP, agent design — I built the fluency personally, wiring up AI agents and multi-model pipelines in n8n, Anthropic API, and OpenAI as a practice. I can whiteboard with a CTO without an engineer in the room to translate.

GTM

Community as pipeline

I run founder-and-operator gatherings in Boston, NYC, and DC. It's how I open doors cold outbound can't — and how my customers find their next hire, investor, or design partner. Relationship capital, compounded.

Built with Claude

I don't just sell AI tools. I build with them.

Paste the role you're hiring for and I'll generate a resume + cover letter tailored to your posting — same Claude-powered pipeline I use for my own applications. Only verified facts from my career. No fabricated stats. No invented customer names.

Claude is tailoring your resume.

Fetching the job posting, mapping it against verified facts from my career, and writing a cover letter in my voice. Typically 30–45 seconds.

Outcomes

What it added up to.

4×

East region revenue growth, 2 years

60%+

POC win rate

400%

DNB consumption growth, 2 years post-deployment

$3M

Largest single deal (TCV)

01
Migrated a public conversational AI platform from on-prem to Couchbase's cloud SaaS — reduced TCO and freed engineering to focus on product. $3M TCV multi-year expansion · phased ramp · multi-departmental contracting
02
Closed a 12-month, 10+ stakeholder enterprise deal that crossed engineering, security, legal, finance, and product. $1.2M ACV land-and-expand · Fortune 1000 buyer
03
Built Couchbase's East region from zero — 4× revenue in two years across five new verticals including digitally native businesses. Authored the GTM playbook other territories adopted
04
Drove DNB accounts to 400% consumption growth in the two years post-deployment. Land-and-expand executed on the actual product, not just the contract
05
Three consecutive years of quota over-attainment at Couchbase. 103% (FY'24) · 107% (FY'25) · 151% (FY'26) · President's Club
06
Before Couchbase: $24M pipeline in under 12 months as Strategic BDR at DailyPay. 110% of quota · President's Club FY'23 · vertical playbooks adopted by the broader BDR team

An Invitation

Looking to plug into the local tech & operator scene?

I host invite-only gatherings for tech and business-minded people across Boston, NYC, and DC. Founders building things. Engineers shipping things. Operators scaling things.

No pitch decks. No sponsors. Just the right people in the same room.

15–40 people, curated
Founders, engineering leaders, VCs, F500 operators
Boston · New York · Washington, DC

Delivering business impact
through technical fluency.