Amandeep Singh — Fractional CDO & Global Delivery Leader
Fractional CDO & Global Delivery Leader

Most programmes don't fail suddenly. The signals were there.

14 years embedded in technology programmes across healthcare, SaaS, and enterprise — US to APAC. I fix delivery systems that are failing, and build ones that hold after I'm gone.

$9M+
Portfolio managed
14
Years in delivery
40%+
Efficiency gains delivered
2M+
Patients on governed platforms
$6M programmedelivered 25% ahead of benchmark
0 Sev-1 incidentsacross 2M+ patients
$0 → $2M ARRpractice built from zero
95%+sprint predictability sustained
US · UK · APACmarkets served
8 → 80+teams scaled and retained
£200K+incremental revenue secured
$9M+portfolio managed
Who this is for

You have a delivery problem.
Not a people problem.

The team is capable. The technology is sound. But something in the system is breaking — governance gaps, communication that fails at the seams, accountability that sits with one person when it should sit with the operating model.

Find out if there's a fit

Delivery is unpredictable

Steering committee hears green. The team knows it's red. Six months in, nothing has shipped on schedule.

AI programme stalled

Proof of concept worked. Production is another story. The programme is burning time, budget, and trust.

Scaling without structure

The team grew from 8 to 40. The delivery model didn't. You need systems, not another senior hire.

Services

Four ways in.
One exit condition.

Every engagement is built to make my involvement redundant. The goal isn't delivery that works while I'm there — it's a system that holds after I leave.

01 Retainer · ongoing

Fractional Head of Delivery

"We have delivery leads. What we don't have is someone senior enough to see the whole system and trusted enough by the executive team to change it."

Two days a week embedded in your leadership team. I run the delivery governance cadence, coach your internal leads, give the CTO genuine visibility into programme health, and build the operating model that makes my involvement redundant over time.

  • Weekly delivery health review and executive update
  • Delivery operating model built to outlast the engagement
  • Internal lead coaching and capability building
  • Risk and escalation management with honest, early signals
02 4–6 months

AI Transformation Programme Lead

"We've committed to the AI initiative. Six months in, nothing has shipped — and we can't explain exactly why."

I take ownership of delivery for AI transformation initiatives that have stalled. Programme governance, stakeholder alignment, risk management, and the user adoption framework that determines whether the AI initiative actually survives contact with the organisation.

  • Programme scope defined, risk-rated, and governed end-to-end
  • Delivery roadmap from proof-of-concept to production
  • Stakeholder alignment and change management built into delivery
  • User adoption measured and tracked, not assumed
03 2–4 months

Agile at Scale Programme Lead

"We have Agile teams. What we don't have is an Agile organisation. Every centre runs differently, dependencies are invisible, and no one owns delivery predictability end to end."

Scaling Agile across multiple delivery centres is an organisational design problem, not a methodology problem. I design and embed the operating framework that connects teams across sites — sprint governance, cross-team dependency management, milestone tracking, and the reporting layer that gives senior leadership a true picture of programme health. Delivered a $6M OutSystems programme 25% ahead of benchmark across four centres using exactly this model.

  • Agile operating framework designed and embedded across all delivery centres
  • Cross-team dependency management and milestone governance in place
  • Sprint discipline and predictability improved without increasing headcount
  • Executive-ready reporting that reflects what is actually happening, not what teams report up
04 2 weeks · diagnostic

Delivery Health Assessment

"Something is wrong with how we deliver. We have the frameworks, the tools, the retrospectives. Projects are still late and nobody can explain why."

Two weeks inside your delivery organisation — sprint predictability, governance structure, team dynamics, risk posture, tooling. Not to audit, but to diagnose. The output is a clear picture of where risk is accumulating and what to address first.

  • Delivery maturity assessment across six dimensions
  • Root cause analysis — the underlying problems, not visible symptoms
  • Prioritised 90-day improvement roadmap
  • Executive debrief and Q&A
Selected Results

Three programmes.
All still running after I left.

Discuss your programme →
Healthcare IT · UK–India · AI
AI delivery for a 2M+ patient healthcare platform

A multi-portal platform serving 4,100+ practices had the technical ambition but not the delivery infrastructure to match its clinical stakes. I rebuilt the cross-border operating model, scaled the team from 8 to 20+, and led AI programme delivery — NLQ interfaces and AI Agent tools — while maintaining zero Sev-1 incidents throughout.

£200K+
Incremental revenue · 0 Sev-1 incidents · 95% sprint predictability
Enterprise SaaS · Multi-centre · Agile at scale
$6M transformation across four delivery centres

An OutSystems enterprise programme spanning four delivery centres was drifting — coordination overhead, governance fragmentation, declining predictability. I designed an Agile scaling framework that unified delivery across sites and delivered the full programme 25% faster than the organisational benchmark. Team retention held at 92%.

25%
Faster than benchmark · four centres aligned · 92% team retention
Digital practice · SE Asia + North America
Zero to $2M ARR — a delivery practice built from nothing

No team, no clients, no delivery infrastructure. Over four years: $2M+ ARR, 15+ concurrent client engagements across healthcare, SaaS, and retail, international partnerships across SE Asia and North America, and a 20+ person team built and operating independently.

$2M
ARR in four years · 15+ active clients · 20+ professionals
95%+
Sprint predictability
sustained
8→80+
Teams scaled and
retained
£200K+
Incremental revenue
secured
3
Markets: US · UK
· APAC

A small number of engagements. Each year.

If what you've read describes your situation, a 20-minute conversation will tell us both whether there's a fit.

How I work

Three things I believe every
delivery leader knows.

These aren't methodology slides. They're observations from 14 years of being in the room when programmes fail — and when they don't.

01

Most problems are structural, not technical

When delivery fails, the team usually isn't the cause. The governance cadence is wrong. The communication layer is missing. Accountability sits with a person instead of a system. Fix the structure and talented teams perform.

02

Embedded is different from advising

I sit in the RAID review. I'm on the steering committee call. I know what the delivery signals actually say — not what the status report claims. Distance is the single biggest constraint in traditional consulting.

03

Every engagement needs an exit condition

I'm not building dependency. From day one, the engagement is designed to end — with a delivery operating model your team runs without me. The measure of success is that you don't need me after.

About

Embedded, not advising.
There's a difference.

14 years inside technology organisations — not advising from a distance, but embedded in the work. Most delivery problems aren't technical. They're structural. Governance that doesn't scale. Communication that breaks at the seams. Accountability that sits with one person when it should sit with a system. That's what I fix.

Across agencies, healthcare platforms, and enterprise SaaS transformations, the pattern is consistent: organisations delivering unpredictably start delivering with confidence. Teams losing client trust regain it. AI programmes that stalled get to production. The changes hold because they're built into how the organisation runs — not dependent on my presence to sustain them.

Working with Vivirhub, Xebia, Aaseya, and others has shown me exactly where delivery systems break — and what it takes to fix them in a way that lasts. That accumulated pattern is what I bring into every engagement.

Background

Based in Mumbai and Pune, India. Serving clients in US, UK, and APAC. MBA in Marketing and Finance. BCA in Computer Applications. 14 years of embedded delivery leadership.

Sectors
  • Healthcare SaaS Aaseya
  • Enterprise transformation Xebia
  • Delivery practice build Vivirhub
  • AI programme delivery Active
  • UK–India offshore delivery Confirmed
Positioning

Fractional CDO for organisations that need delivery leadership installed — not a recruiter-facing CV, not a methodology presentation. A small number of engagements per year.

Newsletter

Delivery Intelligence.

How complex software delivery actually works inside large organisations. Written for delivery managers, engineering leaders, and CTOs who want to see past the frameworks.

Not theory. Not productivity tips. Operator-level analysis from inside real programmes — the signals, the mistakes, the patterns that repeat, and what experienced leaders do differently.

Read by delivery managers, CTOs, and programme directors in the US, UK, and APAC.

Join Delivery Intelligence

Weekly. Every Wednesday. Operator-level analysis of how delivery actually works inside complex programmes. No pitch, no padding.

What you'll read

Four areas. All from inside the machine.

01
Delivery war stories

Real situations from enterprise programmes — what happened, why it happened, and what someone with better pattern recognition would have done differently. These aren't cautionary tales. They're maps.

The steering committee heard green. The team knew it was red.
Why the programme collapsed on week 14, not week 3
A stakeholder decision that cost six months of progress
02
Risk detection before crisis

The signals experienced delivery leaders watch for — velocity patterns, communication frequency changes, the quietly reversed scope decisions. What to measure, how to read it, and when to act.

Five metrics that predicted every failure I've seen
What teams stop saying before things go wrong
False progress: what "on track" actually means
03
AI in delivery leadership

What AI actually changes about how programmes are planned, governed, and executed — written from experience delivering AI initiatives into production, not observing them from the outside.

Why most AI pilots don't reach production
The governance gap that kills AI adoption after launch
What a delivery leader needs to understand about LLMs
04
Global delivery leadership

The realities of managing distributed teams across countries, cultures, and timezones. Specifically the UK/US–India delivery corridor — where most failures are predictable, most fixes are underestimated.

Why offshore delivery models fail — and what works
The communication assumptions that break global teams
Leadership mistakes in distributed engineering organisations

The problems in the newsletter are the problems I fix. If yours is on that list, reach out.

Work with me

One conversation.
You'll know
if there's a fit.

Twenty minutes. Three questions — the problem, what you've already tried, and what good looks like in 90 days. By the end, we'll both know if there's a fit. If there is, a one-page proposal follows within 48 hours.

Accepting engagements now for 2026.
Serving clients in US, UK, and APAC.

Not a fit if: you need five days a week, you're pre-revenue, or you want a methodology presentation. I'll tell you that in the first five minutes.
What to expect
A conversation, not a pitch.
  • You describe the situation — no slides, no prep needed
  • I ask three questions to understand the root issue
  • I tell you honestly whether there's a fit
  • If yes — a one-page proposal within 48 hours
Drop me a note on LinkedIn →

No forms. No scheduling links. Just a direct message.

Not a fit if: you need five days a week, you're pre-revenue, or you want a methodology presentation. I'll tell you that in the first five minutes.