In the world of bids and proposals, there’s a quiet challenge that has persisted for years, one that many professionals will instantly recognise: collaboration, especially with SMEs (Subject Matter Experts).
For Darrell Woodward, this challenge has been front and centre for the past five years. But rather than accept it as “just the way things are”, he’s focused on solving it, by helping SMEs help bid teams. It’s a simple idea, but one with the potential to transform how proposals are created and won.
It’s also a conversation gaining momentum across the industry, with events like Optimize26 bringing professionals together to explore exactly these kinds of challenges, how people, process, and technology can better align to improve outcomes.
The Moment That Changed Everything
Eight years ago, Darrell was commuting to work, listening to an audiobook. As the bus pulled up outside his company’s European HQ, one line stopped him in his tracks:
“Ask yourself: Do you want to work for your own dreams or someone else’s?”
That was it. A turning point.
From that moment, he knew he wanted to go freelance. Not just to work for himself, but to specialise, to carve out a niche in RFP software and bid process optimisation.
Since then, he’s built a career helping organisations select the right technology for their bid processes and, crucially, helping them evolve those processes to fully leverage what that technology can do.
Stumbling into a Career (and Finding a Community)
Like many in the profession, Darrell didn’t set out to work in bids and proposals.
His first experience came as a marketing manager at a small tech firm. The company received an RFP from a major bank, and he was asked to join the bid team.
There was just one problem: no one else had read the RFP. No one knew what to do.
But to him, it all seemed… obvious.
That moment sparked something. He thought he’d discovered a career path that was both enjoyable and oddly underappreciated, something he understood that others didn’t.
Only later did he discover the wider world of bidding: a global community of experts, structured methodologies, certifications, and innovative technologies. It was humbling but also energising. It opened the door to continuous learning, growth, and mastery.
The Hardest Question: “What Do You Do?”
Ask most professionals what they do, and you’ll get a straightforward answer.
Ask someone in bids and proposals? Not so much.
Darrell jokes that explaining his job is his biggest professional challenge. The field itself isn’t widely understood outside business development or procurement and even within those areas, clarity can be lacking.
Add in a niche focus on RFP software and process optimisation, and the explanation becomes even more abstract.
His family’s running joke? He must work for MI5 because his explanations sound like a spy’s cover story.
But beneath the humour lies a real issue: as a profession, bidding still lacks a simple, universal definition. Solve that, and everything, from awareness to career pathways gets easier.
Lessons from Losing
Not all lessons come from success. Some of the most valuable come from the bids you don’t win.
One experience from 2012 stands out.
Darrell was the sole proposal manager in a qualification meeting. By every meaningful criterion, the opportunity was a poor fit, except for one thing: it was high value.
And that changed everything.
Suddenly, logic gave way to optimism. Phrases like “you’ve got to be in it to win it” started to dominate. Red flags were raised but ultimately ignored.
They pursued the bid. And they lost. Twice.
The cost wasn’t just the loss itself. It was the wasted time, the diverted resources, and the hit to team morale.
The lesson? Trust the process. Sometimes, winning means having the discipline to walk away.
The Skills That Matter Most (Especially Now)
In today’s AI-driven world, there’s a growing conversation about skills, what matters, what’s replaceable, and what isn’t.
For Darrell, the answer is clear.
The so-called “soft skills” or what he prefers to call the professional arts are more important than ever:
- Intuition
- Empathy
- Critical thinking
- Problem solving
- Decision making
These are the qualities that elevate a bid from good to great. They’re what differentiate a submission that participates from one that wins.
"AI can support the process but it’s human insight that makes the difference."
Finding and Owning Your Niche
If there’s one piece of advice Darrell offers to those starting out, it’s this:
Keep an open mind. Look for learning everywhere.
Over time, you’ll discover the parts of the job that truly resonate with you, the tasks that energise rather than drain you. That’s your niche.
And once you’ve found it? Own it.
Build your expertise. Share your knowledge. Contribute to the industry. Because in a field as dynamic and evolving as bids and proposals, there’s always room for specialists who push things forward.
Life Beyond the Desk
Outside of work, Darrell’s energy doesn’t slow down.
Based in Thatcham, West Berkshire, he’s deeply involved in squash, playing four to five times a week, organising local leagues, and coaching both adults and GCSE students.
But it’s not just sport that reflects his approach to work. Music plays its part too.
Artists like RAYE stand out to him, not just for their sound, but for their craft. “There’s something compelling about the way she moves between genres, blends modern production with rich orchestral backing, and ensures every song tells a story.” It’s not a bad analogy for great bid writing.
The best proposals don’t follow a rigid formula. They adapt, they build depth, and they bring together different elements, technical detail, commercial insight, and narrative, into something cohesive and persuasive. Like a great track, they’re structured with intent, but delivered with creativity.
It’s a mindset that carries through to Darrell’s professional life: always learning, always improving, always aiming higher.
Final Thought
Bids and proposals might not always be easy to explain, but for those in the field, the impact is undeniable.
At its core, it’s about making smart decisions, telling compelling stories, and bringing together people, processes, and technology in a way that wins.
"Sometimes, the most important move you can make is knowing when not to play."
Catch Darrell at Optimize26: The Global Bid Conference
Darrell will be speaking on day three of Optimize26, live in London, UK. This event is designed specifically for the people who live and breathe bids, proposals, capture, and contracts.
Best of all? It’s completely free.
- When: Day 3 (16th April) | 8:30 AM – 4:00 PM GMT
- Where: 10 St Bride ST, London EC4A 4AD, United Kingdom
Can’t make the in-person? Register anyway! We’ll send the virtual recordings directly to your inbox so you don’t miss a single insight from our expert lineup.
