🎉 You found the secret! Use ↑↑↓↓←→←→BA
CC Ciaran Connolly
Senior Account Executive

Ciaran Connolly

AI & Enterprise SaaS
Sales

Six years selling and deploying AI to enterprises that were afraid of it. I know where adoption stalls, what makes a CFO say yes, and why trust is the only thing that actually matters.

Read my letter → View experience
6yr+
Enterprise AI sales at LinkedIn
25%
Client engagement uplift via AI
15%
Net-retention rise via upsell
<1hr
Transcript → personalised proposal
Reading from your company? — this CV personalizes itself.
Cover letter

A letter to your team

Personal. Direct. Same letter I'd send if I were applying tomorrow morning — just with the right name on it.

Dear Hiring Team,

I'm writing about a Senior AE role at your company. You receive many applications, so let me be direct about why this one is different: I have spent the last two years not just selling AI products, but living inside the exact problem you're trying to solve.

At LinkedIn Talent Solutions, I led the pilot and commercial rollout of LinkedIn Hiring Assistant — an AI product built on large language models — across enterprise accounts. I navigated procurement teams, general counsel, CHROs, and CFOs/CTOs/CIOs. I heard every objection: "How does the model make decisions? Who owns the data? What happens when it's wrong?" I learned, deal by deal, that enterprise AI adoption lives or dies on trust. Not feature sets. Not benchmarks. Trust.

The companies that win the next decade of AI won't have the smartest model. They'll have the most trusted one. I want to be the person extending that trust to the next hundred customers at your company.

Practically, here's what I bring: six years managing complex enterprise sales cycles at LinkedIn — multi-stakeholder, multi-quarter, with Finance, Legal, and Technology all in the room. Direct AI product sales experience, selling LLM-powered tools into organisations nervous about AI. And a design and UX background that makes me unusually effective at product demonstration — I can translate AI capability into language a CFO finds equally compelling.

I'm not trying to get into AI sales. I'm already in it. I want to do it at the company whose mission and ambition I believe in most — and right now I think that's yours.

I'd genuinely welcome the chance to speak at whatever stage makes sense for your process.

Ciaran Connolly
ciaranconno@gmail.com · +353 87 1122600 · Dublin
Experience

How I sell with AI

A decade in enterprise sales, three years deep in AI product deployment. Each role narrowed me toward one thing: building trust at scale.

Oct 2019 – Present
LinkedIn
Talent Solutions
AI Product Sales
Senior Account Executive — Existing Business
25%
Engagement uplift
15%
Net-retention rise
12+
AI pilot rollouts
  • AI Deployment Lead: Drove pilot and commercial rollout of LinkedIn Hiring Assistant — an LLM-powered tool — across enterprise accounts, navigating procurement, legal and C-suite approval to embed AI into core client workflows.
  • Enterprise Revenue Growth: Own full sales cycle for expansion deals across a high-value portfolio, consistently exceeding net-retention targets by 15%.
  • Exec-Level Consultative Selling: Strategic advisor to CHROs, CPOs, CFOs, CTOs, CIOs and CEOs — building ROI models that translate AI capability into board-level investment decisions.
  • Trust-Driven Adoption: Address data governance, compliance and change management proactively — enterprise AI adoption lives or dies on trust, not features.
  • AI Workflow Builder: Built a transcript-to-proposal pipeline using Claude that turns client call recordings into personalised renewal decks in under an hour. Used daily across the wider team.
Jan 2017 – Oct 2019
Vodafone Ireland
Public Sector
Government Accounts
Irish Government Account Manager
  • Primary commercial contact for 150 Irish Government and Public Sector accounts, managing complex procurement environments and long-cycle stakeholder relationships.
  • Consistently surpassed quarterly revenue targets through proactive lifecycle management and strategic upselling across mobile, fixed and integrated solutions.
  • Built reputation across the public sector as a trusted commercial partner navigating multi-year framework agreements.
Jan 2014 – Dec 2016
Vodafone Ireland
SME
Team Leader
Team Leader — SME Sales & Retention
  • Led and coached a high-performing sales team driving new business acquisition and customer retention across the Irish SME segment.
  • Designed and launched targeted campaigns that accelerated product uptake and built a predictable, measurable sales pipeline.
  • Built coaching frameworks still used by the team today.
How I work

The AI pipeline I run every day

Not a concept. Not a mockup. A real workflow turning client calls into personalised proposals in under an hour — built and shared across my team.

01
Client call recorded
30–60 min discovery or renewal via Teams or Zoom. Auto-transcribed.
02
Transcript into Claude
Pasted into a Claude Project pre-loaded with master prompt and client context.
03
Claude extracts & builds
Pain points, stakeholder names, objections, budget signals — all pulled and structured.
04
Proposal pack generated
Personalised email, renewal deck outline, CFO summary, preemptive objection responses.
05
Review & send same day
Client receives a proposal using their own words back at them. Deal velocity increases.
claude_project · renewal_system
# RENEWAL PROPOSAL SYSTEM · master prompt

role = "senior enterprise AE,
        AI & Enterprise SaaS"

extract = {
  "pain_points":    top 3 from transcript,
  "stakeholders":   names, roles, priorities,
  "objections":     price · ROI · timing,
  "budget_signals": any pricing language
}

output = [
  proposal_email(tone=conversational),
  renewal_deck_outline(slides=5),
  c_suite_roi_summary(one_page=True),
  objection_responses(preemptive)
]

# turnaround: <60 minutes from call end
Sample output — RCORP renewal
47 min turnaround
Pain extracted
Time-to-hire in senior roles. "Tight but flexible if ROI is clear." Q2 board review flagged.
Email opener
"Abbie — following our call, I've put together a view of the next 36 months specifically around the senior hire bottleneck you mentioned…"
Delivered
1 email · 1 deck outline · 1 CFO summary · 3 objection responses
Proposal templates

How I build a proposal that closes

Each framework personalised by AI and sent by a human. The client's own language reflected back. The right stakeholder addressed directly. Objections answered before they're raised.

Renewal
36-Month Strategic Renewal
  • Opens with the client's own pain point — extracted from transcript by Claude
  • ROI model tailored to their hire volume and time-to-hire data
  • CFO-facing one-pager built in — Finance & Tech stakeholders addressed separately
  • Preemptive objection responses woven into the narrative
  • Three commercial options — anchored high, landed in the middle
Claude-assisted
New Business
First-Meeting Pitch Framework
  • Opens with a careers-page insight showing exactly where their hiring is broken
  • Benchmarks their time-to-hire against industry data before the first call
  • Structured as a conversation guide — gets the client talking, not presenting back
  • Proof points matched by Claude to the prospect's sector and company profile
Claude-assisted
ROI
CFO/CTO/CIO-Facing Business Case
  • One page only — built for an exec with 90 seconds and a results-first instinct
  • Cost-per-hire model with LinkedIn data overlaid against their salary band
  • Payback period calculated and visualised — no jargon, just numbers
  • Risk section included — answers "what if it doesn't work" before it's asked
  • Signed off as Ciaran, not "the LinkedIn team" — ownership signals confidence
Claude-assisted
Email Sequence
AI-Personalised Outreach
  • Cold email built around a specific trigger — funding round, job posting, exec hire
  • Follow-up references the first email naturally — never "just checking in"
  • Re-engagement at day 14 — different angle, different value prop, same tone
  • All signed "Ciaran" — no corporate voice, no "I hope this finds you well"
Claude-assisted
Live demo

Try the way I use AI

Pick a question or write your own. This calls a real AI model — same tooling I use every day to turn client calls into proposals.

Ask me anything →

Pre-loaded with my CV. Ask why you should hire me, give me a sales scenario, or anything else.

Response
Pick a question on the left, or type your own. Replies stream in real time.
Why this matters

What I believe
about AI in enterprise

These aren't values I adopted when I started applying for AI jobs. They're conclusions I reached from six years in the field.

01
Trust is the product
Enterprise AI adoption doesn't fail because the technology isn't good enough. It fails because the vendor wasn't trusted enough. The best AI loses to a trustworthy competitor every time.
02
Safety and growth are the same thing
The companies winning enterprise AI right now are the ones treating responsible deployment as a commercial advantage, not a tax. I close more deals when I lead with governance, not less.
03
A demo isn't a strategy
Buyers don't want to be impressed — they want to be guided. My job is to make the path from procurement to production look obvious. The "wow" moments come later, after the trust is set.
04
CFOs buy outcomes, not models
No CFO has ever signed a purchase order for "a 70B parameter LLM." They sign for cost-per-hire reduced, time-to-close shortened, headcount avoided. Your job is to translate.
05
Use the product you sell
If your AE team isn't using AI to write their own proposals, they can't credibly sell it to enterprises. I run my pipeline through Claude every day. It's the most honest demo I have.
06
Mission compounds revenue
People stay, refer, and advocate when the work means something. The strongest enterprise sellers I know all sell at companies whose mission they'd describe over dinner. So do I.
Skills & expertise

What I bring to the table

AI & Sales Methodology

  • Enterprise AI Sales — full-cycle ownership of LLM-powered product deployment
  • Complex Sales Cycles — multi-stakeholder, multi-quarter, multi-region deals
  • Consultative Selling — discovery-led, problem-first, outcome-anchored
  • ROI Modelling — translating model capability into board-grade financials
  • C-Suite Engagement — CFOs, CTOs, CIOs, CHROs, CEOs
  • Pipeline & Forecasting — predictable, measurable, defensible
  • Trust & Governance Selling — security, compliance and change-management as the buy

Tools & Platforms

  • Claude — daily user, custom Projects, prompt engineering for sales workflows
  • LLM Product Stack — OpenAI, Anthropic, Microsoft Copilot, custom RAG pipelines
  • Salesforce — pipeline hygiene, opportunity management, executive reporting
  • LinkedIn Sales Navigator & Recruiter — power user, six years in
  • Gong / Chorus — call analysis & transcript-to-action workflows
  • Microsoft 365 & Google Workspace
  • Adobe Creative Suite — design background applied to client decks

Reference

Available on request
Senior Director — LinkedIn Talent Solutions, EMEA
"Ciaran is one of the few AEs in this org who genuinely understands how enterprises buy AI."
Available on request
Head of Public Sector — Vodafone Ireland
"Trusted by every government account he managed. That doesn't happen by accident."
Education & certifications

How I got here

Ongoing – 2026
LinkedIn Mission AI Orbit Badge
LinkedIn Internal Certification
AI strategy & enterprise deployment programme — completed across product, sales and security tracks.
2024
LinkedIn Ascent AI Badge
LinkedIn Internal Certification
Advanced AI sales methodology — applied AI in pipeline management and account expansion.
2024
LinkedIn 30-Day AI Challenge
LinkedIn — Public Cohort
Completed and shared publicly — daily applied-AI challenges in client-facing workflows.
2014 – 2017
BA Graphic Design
Dublin Institute of Design
Visual communication and UX/UI — the design background I bring into every client demo.
2014 – 2017
UX/UI Design Degree
Dublin Institute of Design
User-centred design fundamentals — usability, research, prototyping, hierarchy.
2012 – 2014
Web Design Diploma
Griffith College Dublin
HTML, CSS, design systems and front-end fundamentals.