Executive Mentoring for Investment Technology Leaders

From the best technologist in the room to a trusted executive at the table.

An Charraig Consulting helps technology leaders at hedge funds, private equity, venture capital and family offices close the gaps that hold them back: presence, business fluency and communication. The result is a leader the firm sees as a partner, not a cost center.

30+years of executive leadership in the investment industry
5hedge funds where John led technology
C-Suiteroles held as CEO, COO, CIO and CTO
1:1personal, confidential mentoring
Why "An Charraig"

A steady foundation for the climb.

An Charraig
Irish Gaelic · "the rock"

A rock is what you build on, and what you hold onto when conditions turn. The practice is built on that idea: steady, candid, experienced guidance for technology leaders working in one of the most demanding industries there is.

01

Giving back what took decades to learn

Most great technologists are promoted for technical excellence, then judged on things nobody taught them: how they present themselves, how they speak to partners and portfolio managers, and how they lead through ambiguity. I've walked that road from engineer to CTO to C-suite, and I help others walk it faster.

02

Speaking business, not "geek"

At an investment firm, technology earns influence when it's framed in the firm's language: risk, return, capital, regulators and investors. I help leaders translate architecture into outcomes so their ideas get funded and their voice carries weight.

03

A confidential place to exhale

The buy-side is a high-pressure place to work, and the people can be as demanding as the markets. Sometimes the most valuable thing is an experienced, discreet ear: someone outside the building who understands the pressure and helps you find your footing again.

Who I Work With

Built for the people who keep the firm running.

Whether you are early in the climb or already in the chair, the goal is the same: lead with the confidence and credibility of an executive.

Rising Leaders

Emerging technology leaders

Senior engineers, infrastructure leads, and IT and security managers who are ready for more. You have the technical depth; we build the executive presence, business acumen and communication skills that get you to the next seat.

In the Chair

New and sitting CTOs, CIOs, CISOs & CAIOs

Technology and AI leaders who need to shape strategy, manage up to partners and the COO, lead larger teams and represent technology to investors, auditors and regulators, without losing the trust of the team behind them.

Firm Leadership

COOs, CEOs & managing partners

Firms that want to invest in their head of technology. At your request, I work alongside your technology leader to close the gap between IT and management, so you get a strategic partner and not just a capable operator.

Services

Closing the gaps between talent and potential.

Every engagement is tailored, but the work tends to fall into six areas.

Executive Presence

How you show up shapes how you are heard. We work on bearing, confidence and credibility in the rooms that matter.

  • Presence in partner & IC meetings
  • Personal brand inside the firm
  • Handling pressure & pushback

Business Fluency

Learn how the firm makes money, how capital and risk drive decisions, and how to tie technology directly to those outcomes.

  • Fund economics & operating model
  • Building the business case
  • Budgeting & vendor value

Oral & Written Communication

Clear, concise and audience-aware. From the two-minute update to the board memo, we sharpen how you write, speak and present.

  • Board & management presentations
  • Executive memos & emails
  • Incident & risk communications

Stakeholder Leadership

Navigate partners, PMs, operations, compliance and investors, and build the relationships that turn technology into a trusted function.

  • Managing up & across
  • Influence without authority
  • Leading & growing your team

Confidential Counsel

A discreet, experienced sounding board for difficult people, difficult decisions and the stress of working in this industry.

  • Off-the-record perspective
  • Career & transition decisions
  • Resilience under pressure

Firm-Sponsored Advisory

Engaged by firm leadership to guide the head of technology, bridging the gap between technology and management with structure and accountability.

  • Leadership assessment
  • Development roadmap
  • Progress reviews with sponsors
The Shift

Same expertise. A very different conversation.

The gap between a strong technologist and a respected executive is rarely technical. It's in how the work is framed, communicated and connected to the business.

"We need to migrate to a new OMS and refactor the data layer."
"This cuts trade-break risk and frees the desk to scale into new strategies."
Defending the technology budget line by line
Leading the investment conversation on outcomes and risk
Reporting on tickets, uptime and patches
Briefing partners on operational resilience and investor confidence
Being called when something breaks
Being invited in before the decision is made
The Approach

A deliberate path, one foothold at a time.

Practical and personal, grounded in how investment firms actually work.

Step 01

Listen

A candid conversation about where you are, where you want to go and what's in the way. Everything stays confidential.

Step 02

Assess

Identify the specific gaps, whether presence, business fluency, communication or relationships, using real situations from your week rather than theory.

Step 03

Build

Regular one-on-one sessions, live preparation for key meetings, and feedback on your writing and presentations as you go.

Step 04

Bridge

Turn new skills into standing with the business: stronger relationships with leadership and a lasting seat at the table.

Ways to Work Together

Engagements that fit the moment.

From an individual investing in their own growth to a firm investing in its technology leadership.

For Individuals

One-on-One Mentoring

An ongoing, confidential partnership for technology professionals committed to becoming executives.

  • Regular private sessions
  • Personal development plan
  • Meeting & presentation prep
  • Writing & communication feedback
  • Access between sessions when it matters
Inquire →
Focused

Sounding Board Sessions

Targeted support for a defining moment: a new role, a hard conversation, a board presentation or a career decision.

  • Single or short-series sessions
  • New-role first-90-days plan
  • High-stakes presentation rehearsal
  • Career & offer decisions
  • A trusted, experienced ear
Book a Session →
John Brennan, Founder of An Charraig Consulting
John BrennanFounder & Principal
About John

I've sat in your chair, and I've seen what it takes to rise from it.

John Brennan has spent more than 30 years leading technology in the alternative investment industry. He has led technology at five hedge funds: Highfields Capital, Dawson Capital, Andor Capital, Pequot Capital and Dawson-Samberg Capital. He later served as Chief Strategy Officer at Eze Castle Integration. Across his career he has held CEO, COO, CIO, CTO and board-advisory roles at leading hedge funds and technology firms.

John is also CEO & Co-Founder and Managing Partner of AITEC, the Alternative Investment Technology Executive Club, a private peer community for senior buy-side and sell-side technology leaders. In that role he has spent years listening to what separates the technology leaders who earn a seat at the table from those who never quite get there.

An Charraig Consulting is how he gives that knowledge back. Mentoring has been a lifelong thread, from his work with the Pershing Rifles Company K-8 Alumni Association of Seton Hall University and the active ROTC cadets, to the many technology leaders he has guided informally over three decades. For nine years he served as Chairman of the AITEC Gives Back Foundation, helping raise millions of dollars for veterans' organizations and inner-city youth groups. In 2026 he was a guest lecturer at Fordham University, sharing his experience in investment technology and leadership with the next generation, and he has been invited back to lecture again in 2027.

Away from work, John is an endurance athlete and climber: a six-time Ironman finisher, including the World Championship in Kona, with summits across the continental U.S. and Alaska.

Hedge FundsHighfields · Dawson · Andor · Pequot · Dawson-Samberg
AITECCEO & Co-Founder, Managing Partner
AuthorCo-author, Ch. 9, The Insider's Guide to Hedge Funds (2018)
EducationSeton Hall University, Class of '86
Guest LecturerFordham University, 2026 · invited back for 2027
PhilanthropyChairman, AITEC Gives Back Foundation (9 years)
“We define ourselves by how we face and overcome obstacles.”
John Brennan
In Their Words

Leaders who made the climb.

Technology leaders and firm executives on working with John. Names are kept confidential at their request.

“

John taught me that the room doesn't care how elegant the architecture is. It cares what it does for the fund. The first time I presented to our investment committee in their language instead of mine, the whole conversation changed, and so did my seat at the table.

M.R.
M.R.Chief Technology Officer, Multi-Strategy Hedge Fund
“

We brought John in to work with our head of IT, a brilliant technologist who struggled to get traction with the partners. Within months he was leading the technology budget discussion instead of defending it.

D.L.
D.L.Chief Operating Officer, Private Equity Firm
“

Some weeks I needed a strategy. Some weeks I just needed to vent to someone who had been in the chair. John was always both: honest, discreet and steady.

S.P.
S.P.Director of Technology, Single-Family Office
“

He helped me stop thinking like the best engineer in the building and start thinking like an officer of the firm. Two years later I was named CIO.

K.T.
K.T.Chief Information Officer, Long/Short Equity Fund
“

John marked up my first board memo like a mentor, not an editor. He showed me how to lead with the decision and the risk and leave the details for the appendix. I still write that way.

J.W.
J.W.Head of Engineering, Quantitative Asset Manager
“

As a CISO, I knew the threats cold but couldn't get the partners to engage. John showed me how to frame cyber risk as business and investor risk. Now security is on the leadership agenda every quarter.

A.C.
A.C.Chief Information Security Officer, Global Macro Fund
“

Our technology lead had the skills but not the voice. John's structured approach and regular check-ins with us as sponsors made the investment pay for itself.

R.B.
R.B.Managing Partner, Credit Fund
“

I went from IT manager at an emerging manager to Head of Technology. John helped me see the gaps I couldn't see in myself and gave me a practical plan to close them.

T.N.
T.N.Head of Technology, Emerging Hedge Fund Manager
“

Few people understand both the technology and the culture of the buy-side the way John does. His perspective saved me from at least two career mistakes.

E.F.
E.F.Chief Technology Officer, Venture Capital Firm
“

Before a major operational due diligence meeting with a large allocator, John rehearsed it with me twice. I walked in calm and walked out with the investor's confidence and my CEO's.

P.G.
P.G.Head of IT & Operations, Event-Driven Fund
“

John doesn't just give advice. He gives you the confidence to act on it. My presence in partner meetings is completely different than it was a year ago.

L.M.
L.M.VP, Infrastructure & Cloud, Multi-Manager Platform
“

I was offered a CTO role at a smaller fund and wasn't sure I was ready. John helped me weigh it honestly and then helped me plan my first ninety days. Best decision I've made.

C.H.
C.H.Chief Technology Officer, Real Estate Investment Manager
Questions

What to expect.

Every relationship begins with a no-obligation conversation.

Is this coaching, consulting or mentoring?

Mostly mentoring, informed by real executive experience. Some sessions are about building a skill, some are about working through a live situation, and some are simply about having a trusted person to talk to. The focus is always on growing you, not on doing the work for you.

Is everything confidential?

Yes. Discretion is fundamental in this industry. For firm-sponsored engagements, we agree up front with the sponsor and the leader on what is shared, which is typically progress and goals rather than the content of conversations.

Do you only work with hedge funds?

No. I work with technology leaders across the alternative investment and broader buy-side world, including hedge funds, private equity, venture capital, credit, real estate and family offices.

How long does an engagement last?

One-on-one mentoring usually runs six to twelve months, because meaningful change takes time. Focused sounding-board sessions can be as short as a single conversation before a big moment.

Can my firm sponsor the engagement?

Absolutely. Many firms see developing their technology leader as one of their highest-return investments. I'm happy to speak with your COO, CEO or managing partner directly.

Start a Conversation

Ready for the next step on the climb?

Whether you're a technology leader ready to grow or a firm investing in your head of technology, let's talk. The first conversation is confidential and there's no obligation.

Emailjohn@anc.rocks
LinkedInlinkedin.com/in/jfbrennan-us
Phone720-772-1098
Mailing AddressAn Charraig Consulting LLC
1201 Kings Highway, STE 2, #1063
Fairfield, CT 06824