Would You Rather Be has been acquired!

Phil Hewinson
9 min readJan 24, 2023


We’ve just been acquired by the Learning Curve Group!

They provide education and training courses to about 200,000 students per year to help them in their careers. They have acquired our software and all of our assets, and over the next few months I’ll be working with them to integrate our product into their offering so we can give their students access to our personalised, intelligent career advice.

I know it’s been over a year since my last update! And a LOT has happened. So before I get into how this acquisition came about, let me rewind back to September 2021 and pick things up since my last blog post

10 more product experiments

Between May and December 2021 we ran a total of 26 product, pricing and ad experiments with the goal of driving the ROI (return on investment) on our ad spend as high as possible. We did the last 10 of these experiments between September and December — we doubled our pricing, tested free content and varied our ads and copy. We achieved 99% gross ROI on our ad spend.

We then planned to re-engage the users who didn’t pay, with emails to further drive conversions. So we introduced a contact capture screen before payment to enable us to do that, which we tested at the start and the end of the flow. But we lost 30% of users on this screen, and only had 28% of people opt-in to future emails. Given these poor results, we decided not to pursue the email re-engagement strategy.

While our gross ROI was strong, it wasn’t strong enough to scale with ads. So to continue pursuing a direct-to-consumer offering, we needed to give users more value…

1:1 support

In September 2021 we escaped as a team on our first offsite — to the Peak District. We had a brilliant time over 5 days getting to know each other (some of us had never met in person!), going for walks and enjoying some fun activities like an Escape Room.

Our main focus during the week was a design sprint, focused on how we can better help people change into a career that will make them happy in an economically viable way. We all prepared and presented other products that have inspired us, and then went through a creative process to come up with ideas for enhancing our offering to our users.

The outcome of this exercise was to craft and test a Changemaker Program, designed to help users change careers for £30/month. The program involved an initial call, a personal action plan, regular check-ins and support from our research team. Emma and Laura led on this project and crafted the program. They then conducted a series of user interviews to test and refine the proposition.

We then tested the proposition with an email campaign to a subset of our paying users, asking them to sign up by paying a £5 deposit. Unfortunately we didn’t have a strong enough up-take to give us the confidence in the product-market fit of this offering. So we decided to move our focus away from consumers for now, and towards selling into organisations…

Selling to organisations

We spent the rest of 2021 selling Would You Rather Be into organisations. We focused on schools, further education colleges, universities, career coaches and outplacement companies (that help organisations with redundancies).

To better support these prospective customers, we built an organisation dashboard so they can better manage their clients. This gave career coaches authenticated access to a dashboard allowing them to invite their clients to use Would You Rather Be within a branded experience, and track their results.

We then created a sales process for each customer type. We used LinkedIn Sales Navigator to find prospects and relevant companies, and LeadIQ to get their contact details. We then stored our prospects in Hubspot and used Klenty to set up email cadences to send out a series of emails to them to ask for a meeting. We also used Canva to design PDFs and collateral.

And we had some success. We demoed our product to over 100 different prospects. And we signed up a few schools, colleges, career coaches and outplacement companies. We had some great feedback from career professionals too, including this quote from Joanne Thorniley at the Career Development Institute:

“I think Would You Rather Be is amazing. I see a lot of career software and I can’t think of anything that matches Would You Rather Be — it’s really, really clever. I’ve never seen anything like their Pathways feature before — it’s totally unique and accessible.”

While we had some success, we weren’t quite getting the traction we were hoping for. So at the end of the year I got the team together for a strategy day, and we decided to focus on building out our core product further. And to do that, we needed to raise money…


At the start of 2022 we launched ourselves into fundraising, with the goal of raising £2–4m. This would enable us to scale our team and deepen the value of our product.

Our Pitch

The core part of our narrative was that we’ve solved career matching better than anyone else in the market — we intelligently map every user to one of 500 careers that are right for them, and we’ve validated this across 80,000 users. So the next natural step is to map these users to actual jobs in a hyper-personalised way, and we needed to build out our product and engineering team to achieve that.

We worked hard on our narrative and pitch deck, refining it, iterating on it based on feedback we received from our early pitches, and getting our designer, Josh, to make it look great. The final version is here.

Reaching out to VCs

We then pulled a list of 94 relevant VCs (Venture Capitalists), starting with Crunchbase, and then filtering based on the size of their fund and if they raised it in the last few years, their preference for seed rounds (relatively early funding rounds like ours), their prominence and whether they’ve invested in similar companies. And the key to fundraising is having warm introductions, so we identified 14 VCs that I have personal connections with and a further 60 that we could probably get warm introductions to from our existing investors, Forward Partners, or through founders I know who have been previously funded by them.

And then we started reaching out to them. We carefully crafted a pitch email with 3–4 paragraphs summarising our pitch by stating the problem we’re solving, our solution, progress to-date, what we want to raise and why, and our team. And we sent these emails along with a link to our pitch deck, which we stored in Docsend, as that notified us when investors opened it.


Over the first 2–3 weeks we pitched about 10 VCs. And we got about £800k committed and a clear route to raising £2m.

But the general feedback to our pitch was lukewarm and VCs have been burnt by startups in the jobs space a lot over the past 10 years, so they were hesitant with ours. And during the process of pitching, I started to lose conviction in our product direction towards job matching. The process forced me to go deep into assessing the feasibility of this new product direction, and I had some strong reservations.

A dramatic u-turn

So after a few weeks into the process, I made a dramatic u-turn and decided I didn’t want to take the company in this direction. After all of our efforts to commercialise the business in 2021, I realised that scaling our company independently would be hard. But we had built an amazing product that was creating lots of genuine value for our users as they figure out their careers. So we decided to explore an acquisition where our software could be used by a company that already has scale, which could add genuine value to their users. We realised this would be a quicker way to realise our mission of helping people find career happiness.


Advice & pitching

I’ve never sold a company before. So our first step was to talk to M&A advisors (M&A stands for “mergers and acquisitions”) who could give us some guidance on the process and what to expect. We curated a list of 17 M&A advisors, most of whom came through recommendations in my founders network, and we spoke to five of them. And I spoke to a couple of founders who have experience with this process. This gave us great insight into how companies are priced, how to identify prospective buyers and how we should approach it.

We then curated a list of potential buyers, many of whom we were already in touch with from our push on sales and partnerships back in November. We then worked hard to create custom decks for each prospective buyer, and emailed a carefully crafted pitch email along with the custom deck to each of them. And we were pleasantly surprised by the positive response rate. Practically every prospect replied, and we pitched many of them.


This ultimately led to three offers being made. Unfortunately I can’t share many of the details because we have NDAs (Non-Disclosure Agreements) in place with these companies, and I want to respect the companies we’ve been talking to. But the overall process has taken 9 months, and had some big ups and downs!!

Since accepting the offer from the Learning Curve Group, our general approach was to find and appoint a lawyer to represent Would You Rather Be, work on and agree to a Heads of Terms (a summary of the final agreement, also known as a “term sheet”), notify our shareholders, go through a lengthy process of due diligence (which involved sharing a lot of documents in a “data room”, which is essentially a shared folder of legal, financial and technical documents), scope the integration and then create, agree and sign the final agreement and other documents. We’ve worked with 6 lawyers on our side alone, producing and agreeing over 80 pages of legal documents.

Learning Curve Group

And I couldn’t be more delighted that the Learning Curve Group has acquired Would You Rather Be. They provide an array of education and training courses to about 200,000 students every year. Their courses help students get into a new career or progress in their current career. And many courses are government funded, which means the students don’t have to pay anything to take them.

Our software will be a brilliant complement to their offering, providing personalised career advice to every student as they navigate their careers. We will deeply integrate the experience so that their courses will be baked into our product to help their students navigate to the best courses to help them progress.

I founded Would You Rather Be to make a material difference in the lives of millions of people by helping them find meaningful work, as I shared in my first blog post when I founded the company. And the heart of the company’s mission is to help those most marginalised in society. Learning Curve’s students typically don’t have many qualifications or access to good career support. And we’ll be helping as many as 200,000 of them every year, which will be millions in the years to come. So I’m really excited that our mission will be realised and for the long-term impact that we’ll have through this acquisition.

Thank you!

As my Would You Rather Be journey draws to a close, I’d like to thank everyone who journeyed with me. For those who worked with me to make WYRB a reality — Emma, Laura, Dharmesh, Leo, Josh, Anna, Kent, Georgie, Don, Cat — thank you! For my investors who believed in me and have supported me throughout the journey in countless ways — Forward Partners (Matt, J, Luke and Nic), Nesta, Liam, Philip and Andrew — thank you! For my early customers, especially Eton College and Middlesbrough College, who signed up and adopted our early software before all the features were fully functional — thank you! For my lawyers at Cooley and Avery, and my rockstar accountant, Andy Erasmus at Aston Hughes — thank you! To the team at the Learning Curve Group for seeing the potential in our platform and taking it forwards to help many people find career happiness in the years to come — thank you! And finally to my wife Anita who was my rock throughout the journey of ups and downs as well as the rest of my family and friends — thank you!