Episode 27 ✹ Pre-RFP Strategy and Bid Qualification, with Simon Cuthbert (Arthurian Labs)

The Stargazy Brief ✹ Simon Cuthbert (Arthurian Labs)

Chris Carter (00:08) Hey Simon, so good to see you and thank you so much for being on the Stargazy Brief.

Simon Cuthbert (00:12) Good morning, Chris. Good to see you again.

Chris Carter (00:14) A lot of the questions I want to ask you are really set on your background as a sales leader and a cybersecurity expert and leader in your space. I think it's really good for people listening to hear from people with that background, because you're going to see it from a really specific lens that we need to be seeing RFPs from as well. So one of my biggest questions to you is: what are winning teams, like winning RFP teams, doing differently within that pre-analysis stage?

Simon Cuthbert (00:47) That's a really good first question, and I'm glad you asked it. The biggest differentiator is that winning teams treat the pre-RFP as a strategy phase, not a preparation phase. Losing teams use that time before an RFP drops to gather information. Winning teams use it to shape the opportunity. They're talking to the buyer, understanding the politics, identifying the real problem behind the stated requirement, which is sometimes not quite aligned, and sometimes even influencing how an RFP gets written. By the time the document lands in their inbox, they're not starting from scratch. They're starting to execute a plan they've already built.

Chris Carter (01:28) I love that. I wish I had more sales leaders in the past who thought about it that way. One thing you do talk about is buyer mapping. What is good buyer mapping, and what does that look like in practice?

Simon Cuthbert (01:40) Good buyer mapping goes well beyond the organizational chart, and that's a big mistake a lot of organizations make. You're not just asking who signs the contract. You're asking who has the pain, who has the budget authority, and who are the internal champions. You also need to understand who the blockers are, because that's just as important as who your internal champions are. Why are they blocking? What does each stakeholder personally gain or lose from the decision of going with your solution as opposed to someone else? The best teams map buyers across three dimensions: their role in the decision, their priorities, and their relationship with you. You want to know who you have access to, and who you don't, just as importantly, and who the competitor might already have a relationship with — that's always a driver. A buyer map that's just names and titles is decoration. A real buyer map drives your whole engagement strategy.

Chris Carter (02:40) I could ask you questions about that all day, because I feel like that is one of the most important things people can do within a sales cycle, RFP or no, to make sure they win: to get that strategy correct.

Simon Cuthbert (02:53) The sales teams I've worked with over the years, we've always been very strong on the relationship and understanding. When I look at a sales organization, I look at two parts. I look at the relationship sales side of the organization, and I look at the delivery side. They're two different people. The relationship person is the one who understands the customer, understands who they're talking to, what their pain is, what the real requirement is, and what the blockers are for winning that RFP, or just that sale, even if it doesn't go to RFP. The other side of that are the smart guys, the technical people. They're the ones that deliver. They go in and sit with the technicians and deliver a solution, whether that be a hybrid cybersecurity solution, or a crane that's being installed in a port somewhere in the UK. I only say that because it's something I was involved in once. But the rules are the same. The framework doesn't change. The important thing for any sales process is to understand your customer. If you don't understand your customer, then you're becoming a sales guy. And nobody likes a sales guy. That's fact, unfortunately.

Chris Carter (04:13) You've seen so many of these play out and helped so many people do buyer mapping within the teams that you run. Do you ever see, especially in RFP situations, that they're overlooking specific people they should be talking to within the buyer organization, that they really need to, in order to make sure they win?

Simon Cuthbert (04:35) First of all, when you're having your sales meetings, forecasting meetings, whatever you want to call them, you're asking your team the questions. Who are you talking to within the organization? Are they the right person, or are they the person that you know?

Because those could be two different people. Understanding who the right people are within an organization is absolutely key to winning that relationship. One of the first things I was ever told, years and years ago, was by a chap called David Geyer. There were two people who gave me an opportunity within cybersecurity: David Geyer and Catherine James, two of the loveliest people I've ever worked with. David was the CEO of the company that took me in.

He said, people buy from people. We all say it, we've said it thousands of times, but it was the first time I'd ever heard it. And he also said to me, if you do everything else right, you will never need to sell anything. I think that's really important. Having the ability to understand your customer, understand who within that customer you need to be addressing and introducing yourself to, is absolutely fundamental. So in answer to your question, yeah, some people are overlooked. Some sales guys only want to talk to the senior people within an organization. I strongly disagree with that process.

I want to be talking to everybody that has an input to a technology that we're talking about, whether that's an admin guy who works in IT, or the chief information security officer, right the way through the chain. But the other thing to remember is they are very different conversations. The pain of an IT admin is completely different to the pain of a CISO, and different again to the pain of a CEO. So you need to understand what those conversations need to look like to be able to have them.

Chris Carter (06:25) One thing I suggest to people is, when you're doing that buyer mapping within your organization — who should be talking to them — make sure they can have that conversation. If you have me talk to a CISO, I'm probably going to use the wrong words and not know exactly what they need to hear. I'm just not going to be able to have that conversation intelligently with them. Whereas if you have me talking to a CRO, we're going to be fine.

Simon Cuthbert (06:49) You're absolutely right.

Chris Carter (06:51) So we've focused a little bit on the pre-RFP. Now let's say we've received an RFP and we need to qualify it. What does a really strong bid qualification have in it? And are there any specific things you see people really focus on within their bid qualification that they shouldn't be focusing on? It's a two-part question.

Simon Cuthbert (07:11) I'll probably forget the second part, so remind me when we get to the end. A strong qualification framework answers five things, honestly. Can we win? Can we deliver? Should we win — meaning, is this good for our business? And I'll give you an anecdote on that in a second. What's it going to cost us to bid? And do we know enough yet to make that call? I see a lot of traps.

The ones I see most often are, first of all, revenue optimism — a phrase I've used many times over the years. A team will qualify it because the number's big, not because the win probability is real. Secondly, when you follow that through, is what we call sunk cost thinking: we've already spent three weeks on this, we can't pull out now. In my opinion, people treat qualification as a one-time gate at the start, when it should be a continuous process. Circumstances change.

A new competitor will come in. Your key contact leaves the buying organization. So you should be re-qualifying throughout the bid.

Chris Carter (08:23) In terms of re-qualifying, do you think it's a time thing, like every week we should be re-looking at it?

Simon Cuthbert (08:27) It's a bit of both. You should always have regular update meetings to update your customer with where you are in that process, and to allow them to update you on where they are in that process. That doesn't happen a lot. There are big gaps between talking to the client and not. And if you're not talking to them, I can damn guarantee that somebody else is. Your closest competitor will be on the phone to them saying, well, when was the last time you heard from them? Silly questions like that, but they get into your head. So there should be regular updates, but when there's key information and it's urgent, then you should be reaching out to your client. And your client should be reaching out to you. If you've got a good relationship with them, they should be reaching out to you also. If something changes — somebody leaves the buying organization, or there's a sudden budget change — a lot of the time you don't get notified. But if your relationship is really good with your key stakeholders, they'll come to you and let you know there's going to be a delay on this part of the process because of ABC. The sales process is a two-way street. It's not just sell, sell, sell. It's not "I've got to do all the running." If the client has a good relationship with you, they'll want to come to you for information.

Chris Carter (09:46) That's a really good point. Do they trust you enough, do they like you enough, to actually reach out to you and ask you?

Simon Cuthbert (09:53) I talk about trust a lot in my cybersecurity roles. I'm a cross-parliamentary advisor on cybersecurity and a regular speaker at a lot of the trade events. I was at InfoSec a couple of weeks ago talking about that, and my title was "Trust." That was the word I used, and I used it a lot. Trust on both sides is absolutely key. And not just "I trust he'll do it." It's "I trust you're giving me the information that is relevant to me, not just pre-canned marketing spiel."

Chris Carter (10:28) That's a tough one. In terms of proposals, when we actually do start writing our bid, how do we build trust in that proposal? Is it being clear and to the point, like you're saying, and not just putting in your pre-written content and sending it over? Is there something we should be doing to build trust within our bids?

Simon Cuthbert (10:48) When we're talking about bids, it's usually a customer we have not had an interaction with previously. Let's take an RFP that has come out. The chances are you may not have a relationship with anybody within that organization, so you're starting from the ground up. And in a lot of instances, once that bid has been released, you can't speak to anybody within that organization about that bid — especially public sector in the UK. So you need to rely on your PQQs, your pre-qualification questions.

You need to be able to articulate those questions in such a way that you stand out from the rest. Not "what's the value of this," "when's the implementation date." You need to be asking searching questions that are going to stand out and make the buyer think, okay, these guys know what they're talking about, because they're asking the relevant questions. That will help to build the trust. Then you get to the stage of bid/no-bid, and you decide, actually, we can put a strong proposal in here. The proposal writing itself can build the trust. Using terms and phrases that the client understands, using real-life case study examples, being able to pull those together and put them into your bid, will help build that trust. I

t's what I call trust at arm's length. They don't know you, you don't really know them, but you're trying to build a remote relationship without having the ability to actually talk to somebody. It's a fine line. It's a difficult skill. And that's one of the reasons — without wanting to sound like a sales guy — that we built Bid Manager. We will build the draft for you, but the warm-blood asset is fundamentally key to being able to win those proposals: reviewing it and then making the manual, human changes that will build more context in, over and above what we've already given you.

You never get anybody who wants to put a 100% AI bid in; they're never going to win it. You need to be able to take those pre-qualification answers and integrate them and create a response that is going to be relevant to that customer.

Chris Carter (13:05) Absolutely. Going back to bid qualification, just really quickly, I want to know if you've seen a difference in revenue attainment from the organizations that use bid qualification versus the ones that don't.

Simon Cuthbert (13:16) The simple answer is yes. But that would make a really boring podcast, so I'll give you a bit more of an answer. The data from our customers makes this stark. Teams that have a disciplined qualification process don't just win more, they win more efficiently, which is key to what we do and how we help our customers. Winning more is key to any bid team being more successful. They're not leading bid resource into no-hope pursuits. Everybody's done it, and everyone will continue to do it, because commercial guys will get involved and say, let's bid on it, whether we're going to win or not. The win rate impact is real, but the cost-of-sale impact is just as significant. A team that stops chasing three bad bids a quarter and redirects that energy into one or two well-qualified opportunities will outperform every time.

Chris Carter (14:09) I'm really looking — with the survey that we're doing, and I'll link it below — I'm hoping to show that with data. You and I know that to be true, because we've seen it in our own lives and our own work, but it's really good to have data to back it up. I genuinely believe that's true. So we've gone through the cycle: the pre-RFP, the qualification of the RFP. Okay, we've qualified it, we're going to go. How can teams then create a really good story for their bid, even before they start writing?

Simon Cuthbert (14:42) I like that question. Story has to come before the writing. You can't just start writing. It's like any good story. When an author writes a book — I've written a book on one of my hobbies outside of this world, one of my passions — before I put pen to paper, I thoroughly researched and wanted to have everything set out in my mind and in front of me, in terms of how I wanted this to come across. If you want to write a coherent bid, the mistake teams make is treating the narrative as something that emerges from the content. It doesn't. It has to be built deliberately. The way I think about it: before anyone writes a word, the team should be able to answer three questions. First, what is the buyer's real problem?

Not the stated requirement, the actual problem underneath it that has resulted in the requirement. Second, what is our distinctive, unique answer to that problem? What can we bring to the table that no one else can, that's going to make us stand out and deliver a strong proposal? And third, being able to deliver a story of why we're the only credible team to deliver that. If you can't answer those three things in plain language, then you're not ready to write. When you can, everything — the executive summary, the section themes, the proof points — will all tie back to the central story.

Chris Carter (16:05) Finding that differentiator is a really tough one. But if you find it, then you're going to be way ahead of everyone else. One other thing I want to say, because a lot of people don't have a technical writing background: one of the first things you're taught is to put an outline together before you start writing. It helps get your brain to put it all together, and you know where you're going. And if you're working collaboratively, everyone else is going to know where you're going and where they need to go. So I'm glad you brought up the outline part.

Simon Cuthbert (16:36) It also goes to emails, as a side note. I can generally tell when an email has been well thought out before it's been written. And on the flip side, it's very easy to see an email that has just been written with no real thought going into it at all. I'm talking about sales. You have to build a structure into a sales email. And it's the same as the PQQs in an RFP. You don't just ask a one-liner — give a reason for asking your question.

Chris Carter (17:07) You know what, I've never heard anyone say that before, giving a reason for the question. I feel like if people were to do that, procurement is a lot less likely to say no, or to say yes and then not give you any background.

Simon Cuthbert (17:21) Context behind any question will generally glean a better response. And also, make sure it's an open question. The amount of PQQs I've seen over the years that are yes/no answers — what is the point of asking a closed question? Then you expect the client and buyer to elaborate on it without you asking them to, and then you'll go back with more PQQs. You said yes — what do you mean? Complete waste of everyone's time and energy. Make sure your PQQs are succinct but also searching, to make sure they understand the question you're asking, which will enable them to give you a response that is clear and coherent.

Chris Carter (18:02) Well, you've just added a new best practice to my proposal process.

Simon Cuthbert (18:05) Glad I can help.

Chris Carter (18:07) So we've got everything together, we're ready to go. Now we're going to talk about software, because of course I love talking about software. Where should teams be using proposal or bid software, and where should we just be using humans? Where is that mix? Where is that dividing line?

Simon Cuthbert (18:24) The reason I launched Arthurian Labs is because it's something I feel really strongly about: the interaction between what we call cold-blood asset and warm-blood asset. The difference between AI and people. There is a fundamental difference. I've always looked at technology through the eyes of enablement. Technology should be an enabler. It shouldn't be an inhibitor, and it shouldn't be a replacement. It should help people to do their work.

I'm not talking about just proposal writing — AI in general. The tools themselves should be doing the heavy lifting on the intelligence and the synthesis: pulling together past performance, competitor signals, compliance matrices, buyer research, so that the proposal experts can then spend their time on what only a human can do, which is make a judgment, build relationships, and write the narrative. The proposal expert's value isn't in reformatting last year's case studies or building a compliance checklist at midnight.

It's showing that the buyer's procurement lead was burned by a failed implementation two years ago, for example, and that needs to be addressed head-on in the methodology section. Tools accelerate the groundwork, people make the strategic calls. The risk is when teams use AI to replace thinking rather than to create more space for it.

Chris Carter (19:49) I feel like you can really tell when people used AI to replace thinking. You'll probably be able to fool people who aren't an expert in the subject. But if you're trying to convince somebody to purchase your tool in a way that's going to help them, they're going to know.

Simon Cuthbert (20:03) I think, undoubtedly. Some RFPs are now written by AI, which I think is too early to be doing. Some people are incredibly lazy and use AI in completely the wrong way. I can give you some real-world examples from the last two weeks. I won't mention names, I won't mention departments. A public sector tender was released in the UK. I'm involved in an AI platform that would replace the likes of ChatGPT, Copilot, Claude, and so on, and we've done some quite deep research with that particular platform.

I built a prompt — three, four, maybe five lines — that I put into this platform. I asked it to go out and look for responses to a particular tender. I had the tender reference number, so I put that in, I put the department in, I put the title of the requirement in, and I asked it to go out and look for responses that would be my competitors'. It went away and came back — 10 to 15 minutes, I think it was — and it had given me two full responses. Two full tender responses, where competitors had put the RFP into Claude and Claude had written a response for them. Don't get me wrong, it was a dreadful response.

But the important thing to note is it also included all of the competitors' information. People forget that once you've put stuff into these large language models, it's getting spat out at the other end. It doesn't just use it once and then rip it up and throw it away and forget all about it. It uses it to build future responses. So with the right prompts, you can go back and find that information. Organizations that do that are doing a number of things. They're making their own business weaker.

They're effectively causing huge amounts of data security leaks within their organization, and potentially GDPR breaches as well, depending on what they're doing. Organizations need to be far more in tune with the dangers of putting your information out into a public platform, compared to using one that is behind closed doors — one where it doesn't feed into a large language model, doesn't educate the large language model. It just takes your information and uses it to give you a response that is relevant to your business.

Chris Carter (22:50) What I'm surprised about is some people don't even do the very basics — like if you're using Claude, for example, they don't even turn off the little toggle that says "train Claude on your data." Just toggle it off.

Simon Cuthbert (23:03) Nine out of ten people won't. They'll just put it in, and that information is there, and once it's there, it's there. There is a current case in the US at the moment about somebody who has written a novel using Claude, and the argument is who owns the IP. I think that's going to be a very long, very drawn-out, very expensive court case, and the only people who are going to win from that are the lawyers.

Chris Carter (23:27) Yeah. And also, don't write a novel using ChatGPT or Claude, because I can tell, and I hate it.

Simon Cuthbert (23:34) Yeah. Use your brain. But does that answer your question?

Chris Carter (23:40) That answers my question. That goes on to my next question, though. Obviously you have a very rich background in cybersecurity — you spoke at InfoSec, that's been a lot of your career. So if I'm a proposal leader and I don't want to be that person putting all of my company secrets and IP into Claude, what should I be asking a vendor — an AI-specific vendor — to make sure I'm going to be using secure software, and I'm not going to be causing these problems for myself or my company?

Simon Cuthbert (24:09) That's a question that should get asked all the time. And you're right, it's something I talk about at InfoSec and a number of other cybersecurity and security events and forums that I'm involved in. There's a lot of, how can I put it, theatre around AI and the AI space at the moment. Vendors are using the right words without any substance behind it. At InfoSec a couple of weeks ago, the majority of vendors there were "AI this, AI that, reduce your risk with AI, AI threat detection," when the reality of that goes against everything I think AI is. So the questions I push every proposal leader to ask: where does my data go?

And it goes back to the point — is it used to train models? That needs to be asked. What happens to the content that I upload? Is there a way for me to border that content, so nobody else gets access to it, so I can lock that down? Always ask for penetration test results. Ask to see them, don't just ask what they are. Pen testing is fundamentally important. Little side note: most organizations do an annual or biannual pen test. Personally, I think that's a complete waste of time. I think you need to have continual pen testing — literally every week, every couple of weeks, maybe, dependent on the amount of data coming in and out of your organization and the size of your organization. Sometimes you need to have pen tests daily. It sounds extreme, but continual pen testing throughout the year is far more effective, and actually far more efficient, than pen testing once a year.

Unfortunately, certain regulations say you only have to pen test once a year, so that's what a lot of organizations do. We are now seeing a lot of companies taking it on their own back, and at their own expense, doing far more regular pen testing, because they understand that the data is the lifeblood of organizations. If a breach occurs, it's going to cost them millions, tens of millions, sometimes hundreds of millions to get that back to where it was. We're talking lots of data, lots of revenue, lots of reputation, shareholder confidence, shareholder value going down — lots of different things. What else? Where does your data reside? What's the data residency policy? It should matter to clients in the UK: is my data stored in the UK or in the EU — which EU is absolutely fine, by the way — or is it stored in the US? Is it stored in Israel? Is it stored in any country outside the UK and the EU? And most critically, I think, is what are the human access controls? Who inside your vendor can see my content? That's really important.

Chris Carter (26:58) I'm just going to write all those things up and remind everybody to ask those questions. I know if they're in highly regulated industries, they probably are working with their CISO to ask those questions — there's no way they're going to purchase the tool otherwise. But a lot of the people listening to this aren't in highly regulated markets, so they're not going to be asking those questions. So, perfect.

Simon Cuthbert (27:19) And they should still be asking them. Whether they're regulated or not, they should be asking them, because if they're not asking those questions, and your supplier is unable to answer them, then that should raise a whole myriad of different questions.

Chris Carter (27:35) So obviously you see proposals with leaders at a wide variety of companies. Within their career, what should they be focusing on right now to be ready for the future — the near future — what's to come with RFPs and proposals?

Simon Cuthbert (27:49) Three things, I think. First of all is data hygiene. Data hygiene is fundamentally important. Good data in, good data out; bad data in, bad data out. The teams who benefit most from AI are the ones whose institutional knowledge — win themes, case studies, past bids, all the lessons they've learned — is captured and structured. If it's all in people's heads or buried in email chains, you can't leverage it. So you've got to start building a library, a library that is accessible to the right people at the right time.

Secondly is process clarity. AI tools will amplify whatever process you have. If your bid process is chaotic, AI makes it faster chaos, if that makes sense. Teams need to nail down what their workflows are — qualification gates, review cycles, sign-off points — so that when you introduce tools, they're accelerating something that already works. And thirdly, and this is probably the one I think most people underestimate, it refers back to something we spoke about earlier, which is story capability. As AI handles more of the content production, the differentiator will increasingly be the quality of thinking and the narratives that humans, the warm-blood assets, bring to the table. T

he proposal leaders who invest now in sharpening their strategic storytelling, their buyer insight, their ability to build a more compelling case — they're the people who are going to become more valuable as these tools get better and better. They're not going to become less valuable.

As I said earlier, all of these tools should be viewed as an enabler. I've had many conversations with bid teams and bid managers — interestingly, not chief revenue officers, they all love the idea — but a lot of people are scared of using tools because they don't understand them. They think it's going to take their job. It's not. It's going to enable you to be more efficient and do your job in a better way than you're currently doing it. That's going to free you up to do more relevant things. And that's what technology should do.

Chris Carter (30:04) I was reading a CSO report from Gartner this morning, and it said less than one percent of layoffs this year have been because of AI. So don't be afraid, don't let that hold you back. I'm completely with you. Okay, Simon. So let's say people listen to this, they resonated with it, they want to connect with you, they want to find Bid Manager Pro. Where can they find you?

Simon Cuthbert (30:25) We've got a pretty cool website. Reach out to me on LinkedIn. I'm quite vocal and, again, opinionated on LinkedIn on a number of different subjects and topics.

Feel free to reach out to me if anybody would like a trial of Bid Manager Pro. I'm blown away by what our CTO and his team have built. I think there's nothing like it in the marketplace that is so comprehensive and so beneficial to bid teams right now. Being able to put a proposal into a platform and have it analyze it and give you a bid/no-bid percentage weighting within 30 seconds is astonishing.

I talk to customers and prospects and ask, what do you need, what are you looking for out of these platforms? The reoccurring theme was: I need to save time, I need to be more efficient, and I need to be able to do more with less. One of our customers tested the platform and came back to me saying it's great, but our budget has been cut. I said, it is what it is. If we can help you, then let me know. About a week or ten days later, she came back to me and said, we have put a compelling case together internally to use Bid Manager Pro. Even though our budget has been cut, the board see that making this investment is going to help us perform our roles with those budget cuts. So nobody's been made redundant. Everybody's been asked to do more, but they're using Bid Manager Pro to make themselves more efficient in what they're doing. I love that story. It's exactly what we're here to do.

Chris Carter (32:17) That's a powerful message.

Simon Cuthbert (32:18) Imagine getting an RFP in via email, forwarding that email to Bid Manager Pro, and getting a response within 30 to 60 seconds — depending on the lag of your email — saying you've got a 78 percent bid percentage. And by the way, this is where you're strong, this is where you're weak, these are your gaps. That's what we deliver. Imagine how many more proposals you can put through in that time.

Chris Carter (32:52) It's not even about more in that case. One of the most powerful messages there is that if you get a really low score, then your team can be focusing on the ones you should be bidding on, because you've just gotten a really good reason of why not. You can bring that up to your CRO or CISO and say, hey, we've got some issues here. Or maybe you see those gaps and you say, you know what, we can probably close those gaps.

Simon Cuthbert (33:14) It takes out the emotion as well. It removes any emotion from departments and sales leaders like I used to be. I've done it so many times and upset bid teams so many times, saying I think we should still bid for it, it's a big number, it would be great if we could win this — and the technical team is saying we haven't got a chance of winning. Bid anyway, because we've got to be in it to win it. The sales directors and account managers as well — I was terrified of losing an existing customer because a bid has come out. You can go to them and say, look, what they're asking for, we just cannot deliver. But let's look at this one, and we can deliver on this.

Chris Carter (33:53) The emotion that comes into these decisions is huge. For me it really hasn't ever been with the VP of sales or the CROs — they tend to be like, yeah, that's a bad one, we shouldn't be doing that. But when it comes to AEs, my gosh, it's a devastating conversation to have with them. I've seen them cry before. But when you do have that data, you do have the gaps, you can make next steps, you can make plans — whether for this RFP or for the next time when they come around. You can see where the gaps are now, so you can fix those for later. I love that. I'm going to put all of the URLs, everything below, so people can find you. Simon, thank you so much for being on the Stargazy Brief, and we'll see you again.

Simon Cuthbert (34:22) Absolutely. I look forward to it. Thanks for your time.