Award entries are part CV, part pitch, and part confession. Rachel Hayward has spent over a decade helping businesses get all three right. Rachel Hayward, founder of Ask the Chameleon, is an East Midlands grant, tender, and award writer. She speaks to Debbie Gilbert about starting her business, helping her clients’ successful applications, and how she has become a multi-award winner herself.
Winner of the Best Solopreneur Award at the inaugural Best SME Awards, Rachel explains how redundancy from the charity sector led her into bid writing, and why she has chosen to stay a solopreneur rather than scale up. She has championed small businesses through the FSB. Rachel also discusses how entering awards allows her to better understand the process.
Crucially, she exposes the dangers of relying on AI for entries, and why she believes human judging will always matter more than automated scoring.
About Rachel
Rachel Hayward is Managing Director of Ask the Chameleon Ltd, the award-winning bid writing and procurement consultancy helping SMEs, charities and social enterprises compete, and win, in markets dominated by much larger organisations.
Since 2015 she has secured access to more than £192.4 million through successful bids, frameworks and tenders, including £4.6 million in charitable grants. As a micro business owner herself, Rachel understands what it takes to compete in a bigger game.
Her expertise spans public sector procurement, grant funding, strategic bid writing and award submissions, including the King’s Awards for Enterprise and Chamber of Commerce Awards. She recently led the Ducks in a Row crowdfunding campaign for Trent Rowing Club, raising £31,140 in memory of her late father, the club’s President for over 30 years.
Her mission is simple: to prove that size should never limit ambition. With the right strategy, even the smallest organisations can compete – and win – in the biggest games.
{2:25} Why Rachel started Ask The Chameleon.
{3:54} Where did the name ‘Ask the Chameleon’ come from?
{5:14} How Rachel built her client base.
{7:00} A conscious decision to remain a solopreneur.
{9:18} Rachel’s efforts to support other small businesses.
{12:03} How Rachel approaches clients requiring award-entry support.
{16:05} Rachel’s own awards journey.
{19:12} The dangers of using AI for award entries.
{22:36} How to make your award entry stand out.
{26:55} What’s on the agenda for the next few years?
{28:35} Rachel’s tendering business.
Connect with Debbie at: https://thebusinessawardsshow.co.uk
Connect with Rachel: https://www.askthechameleon.co.uk/
LinkedIn: https://www.linkedin.com/in/rachelhaywardaskthechameleon/
https://www.linkedin.com/company/ask-the-chameleon-ltd/
Facebook: https://www.facebook.com/askthechameleon/
Instagram: https://www.instagram.com/askthechameleon/
