Inside Modern Bid Management ✹ A Conversation with Oliver Streams and Elliot Easton from Tendium

Christina Carter (00:00) Yeah, thanks so much for being on the podcast. So I really wanted to talk to you both because you have a really unique position, because you both work at a tender company, but you also, Oliver, you run a bid team and Elliot, you respond to RFPs on behalf of Tendium's clients. So it's a really unique situation. And I think a lot of people who are listening to this podcast are in somewhat similar situations because they are like you, they're working for a bid consultancy who are responding to their clients' RFPs. So it's going to be a different industry, different company every single time. Or like Oliver who is managing a team for a bid consultancy.

Buyer Behavior and Misunderstandings

Christina Carter (00:45) I'm wondering, when you manage bids, especially for enterprise SaaS customers, like, what patterns do you see in how buyers behave and what do they often misunderstand about client-side decision-making?

Elliot (01:01) I mean, would say it's part and parcel of being a bid manager is being a good stakeholder, engager and being able to really manage your, expect it or manage the expectations. I think a lot of the time I'm as much a sales advisor as I'm a bid manager and trying to not educate because that's maybe a bit too strong, but guide and softly positioned bid says go or no goes because a salesperson or a sales rep who I'm engaging with who's bringing me an RFP might not have the same level of understanding of how the buyer is going to evaluate the bid, what it means to be non-compliant. I think the main issue I see from our customers is a willingness to proceed even in bad circumstances. and needing to play the bad guy in a way coming into a meeting and sort of saying, look, I understand that this is a great strategic, strategic sort of opportunity for you. could fuel the business for the next two years, but you have no chance of winning.

So I would say that role of being the authority in the room to sort of say, let's not do this. Like this is not the right thing, even when it impacts me financially, right? And like our team benefits from doing more, but we need to maintain a strong relationship with our clients as well as guiding them in best practices and also being transparent

Christina Carter (02:26) Yeah, yeah, there is a big difference, especially in the EU space. I know that almost every single proposal and bid person has been in that same situation, whether they're in-house or, working for a client. Having those really tough go-no-go conversations, I think I have probably made salespeople cry when they know I'm going to be in those calls because I am quite tough about them. But of course, you have to maintain like a really good relationship with your clients as you're doing that. I know many of the people listening to this are in the exact same situation. how do you if let's say you get a really I guess really poor fit RFP or ITT that you know you're going to lose. What do you do? Like how do you maintain that relationship but still you know guide them towards the right decision for them?

Elliot (03:18) For me, it usually starts with listing, risks and liabilities, both for them and then for myself as well. And explaining to them that, look, we don't have this information. You don't have this information. This is not areas where you are compliant. These are the risks that you be faced with if you proceed.

I know it's not a very fun answer to have, but it depends on the client and who they are and how big they are and what sector they're in. You know, if it's a very niche product and we're looking in the private sector, there might be wiggle room.

You might be able to sort of qualify something, even if my gut feeling isn't, all this is going to be a chance of success. In the public sector, I think it's easier to really show a clear yes/no breakdown. And one way I've done that in the past, especially in the public sector, is have an initial meeting with my client. Outline questions that they are curious about, concerning blockers that I know are going to be an issue. Phrase these in a way which makes sense.

Put them to the buyer and essentially wait for the buyer to respond to the Q &A period to then return these to my client and say, look, they're not going to accept any workarounds. They're not going to accept any wiggle room. Like you're going to have to play by these rules and the client typically after a while, then we'll relent and say, okay, yeah, maybe, maybe we'll find something else. I think from our internal end though, in terms of like how we work with our customers, I mean, a lot of it is about limiting our liability, our risk and make sure that like the service we deliver is always qualitative. Right. I mean, we consider ourselves like a partner to our clients rather than like a full outsourcing, right? So I think the fundamental thing of any partnership is communication, being able to communicate openly, you need to be able to have trust. I need to be able to voice my concerns and have them actually understood and seen as actual concerns and not just as someone who doesn't want to go grow business.

And that means that, from our expectations on our client, we expect a lot of, touch points. We expect being kept in the loop and almost being regarded as like an extended team to their internal organization, rather than just, the consultants on the side doing the bids. And really, I mean, to introduce that this partnered perspective that we want to go for in almost all instances, we sort of...work on the premise that shared systems, shared documentation, shared information, like transparency and open see between us so that they can have access to our evaluation models, to our assessment, to our risk assessments, to our liability assessments.

So that they feel that, you know, we're working according to their premises rather than we're working from a shady consultant in the background who's just coming in and saying, no, yes, no, and then charging them a fee, right?

So I'd say that's usually how I'd handle those negotiations or conversations.

Oliver Streams (06:20)

I was going to build on Elliot’s point there. I think it almost comes back to how we structure the deals in the first instance as well. We want to be incentivized in the same way. We don’t want to be incentivized to do volume irrespective of whether it’s a good fit. We want a good chance of winning. We want to structure the deal so we submit good volume where it’s relevant, but we also want to submit with the best chance of winning. So we’re all on the same page—we want to win.

Christina Carter (06:49) Yeah, fair enough. That kind of goes to my next question. Obviously, you don't want to just respond for your customer; you don’t want to just respond for your clients. So I’m curious what a healthy and modern client–vendor bid relationship looks like right now. And I want answers from both of you, but Oliver, if you could give me your opinion first.

Oliver Streams (07:11) Echoing what Elliot said previously, it’s a partnership rather than a straight outsourcing. We want to act as an extension of their team—not something completely separate. And as part of that, the communication, transparency, and clear visibility into how things are working on our end tie into the overall process.

Christina Carter (07:23) Yeah.

Oliver Streams (07:32) Where we’re able to take the role of almost a project manager and treat each response as its own project, the clarity is there. Everyone’s on the same page, and that’s really important—the visibility in the processes, the decisions, the outcomes.

Christina Carter (07:51) So basically you start out right from the beginning with: “Here’s where we fit. This is what we expect from you. This is what we’re going to do.” You just set it up right from the beginning—that.

Oliver Streams (08:00) Yeah. And I think one of our key things, especially for our larger enterprise customers—because we’re working with different account executives and different salespeople on every single RFP—it’s essential for us to have that buy-in from the very beginning so that each individual has some skin in the game.

Whether that’s via messaging—preferably via a call—we get in front of them face-to-face, explain how things are going to work, and make sure they’re invested. Early on, when we were still figuring this out, we didn’t always stick to that process. And we found ourselves in situations where we'd put hours of work into a bid, and the salesperson thought it was complete outsourcing. Then, a few days before submission, they weren’t ready to provide what was required. Ultimately, you can miss the deadline, which is the worst-case scenario. So yeah—it’s really key.

Elliot (08:56) Yeah. I’m not going to repeat everything you said, Oli, because I obviously agree. I’ll build on it. Especially in enterprise SaaS, bids offer you an invaluable resource for outlining technology roadmaps. If you're targeting a certain sector or region—say medtech—bids may surface areas you want to consider adding to your software.

I often sit down with more technical individuals who aren’t working on the RFPs themselves, just to offer insights like: “This is the volume of data we have from previous engagements. Here’s what would benefit your product and increase your chances of winning.” That’s another level of partnership. We offer bid services and RFP services—but we also offer more. We can provide data-driven insights and consistent feedback on how you're performing in the market and how we're being evaluated, public or private.

Christina Carter (10:11) I appreciate that. I’m wondering what your advice would be to a bid consultant who often gets into these situations where they start meeting with a new client, start responding for a new client, and they’re just not getting the level of feedback or even respect from their client when responding to RFPs.

Elliot (10:33) That’s a tough one. The easy answer is: stick at it. Continue to be loud and vocal. Stick to what you know as a bid manager—play to your strengths. Try to align yourself with key stakeholders.

Christina Carter (10:35) Yeah, it is tough.

Elliot (10:55) We often have contact with key stakeholders within client organizations who become our internal champions and expand what we offer. Sitting down with an AWOL account executive who’s brought me an opportunity and says, “This is going to change the business,” and then I have to chase them because they’re not adding the details I need or aligning me with the right people—it’s something I face every day.

There’s no perfect solution, but being vocal, consistent, and directing communication helps. Finding that key champion is huge. As Oliver said—consistent messaging, calls, interfacing with your customers as much as you’re doing the bid work. You want to build that partnership so it’s returning business and enabling faster, smoother ways of working.

Christina Carter (12:00) Yeah, I agree. I know many people are facing these situations every day. So it’s good to get your take.

We just spoke about what your client relationship looks like and how to manage that. Then there’s the layer that’s always existed—but now with added tech. How do you strike the right balance between automation in proposals and the hands-on experience of responding to bids for clients?

Elliot (12:36) It’s largely based on what I’d call a common-sense approach. It might seem easy to include automation tooling and productivity software in a bid workflow—but that only gets you so far. Yes, I can automate my bid work, but ultimately I have to remain hands-on to ensure the context of the tender is clear, the customer strategy is clear—where are we going? That all feeds into how I use automation tools.

A lot of actual bid work, especially in software, is production of content that can be quickly managed. The real cornerstone is understanding how we want to produce it. I spend a lot of time with customers understanding where they are now, their trajectory in three years, where they’re expanding, how we can position their response to get them there faster. What drivers they see as critical.

Then I take that context and feed it into the tools—the productivity tooling and automation AI—so they work in the right way, not just: “Shove it into ChatGPT and say ‘write me a bid.’” That won’t help us.

Christina Carter (14:15) Right. Do your clients want you to come in and guide them on how to start using automation? Because it’s still relatively new and it’s changing rapidly.

Oliver Streams (14:34) I suppose with our specialism in SaaS and software, that uniquely positions us. Our customers want to use AI and automation within the products they're selling. When it comes to bidding, I split it out. For us, automation enables us to scale and be more efficient—but ultimately, the relationship is key. You can’t automate the relationship. It’s face-to-face. It’s done by individuals.

If you start showing your customer reels of automation and lose that human touch, pushing the relationship further away, that would be detrimental to the engagement.

Christina Carter (15:38) And I think a lot of bid people would agree with you. I’m also curious because both of you are embedded in the EU tender space. And what they're doing in the EU is aligned to what the U.S. public sector is doing—using AI to shortlist bids. What are you seeing?

Elliot (16:02) Although we’re based in the EU, I work globally. I spend a lot of time on bids—public and private—in APJ, ANZ, MENA, LATAM, even NAM.

From the evaluation side, it's something that—now, from the Tendium side as a big tech enterprise customer—we understand differently. It aligns with a more structured way of evaluating bids. It has its detriments. It opens the door to very rigid evaluation models. I don’t think the EU has yet found the balance between manual human evaluation and AI-assisted evaluation of tenders.

Oliver Streams (17:11) Adding to that—over the past few years, I’ve seen a shift. A few years ago, people wanted to push out glossy corporate marketing materials as part of the bid. But AI evaluating responses is not interested in glossy marketing. It’s rigid. You get a hard score for price, a hard score for functionality. It’s a tick-box exercise, not a full business-wide subjective evaluation.

Christina Carter (17:51) Yeah, and because you were saying the relationship is still important—how do you structure your response to get shortlisted or meet criteria to pass the AI reviewer?

Elliot (18:07) This might be very niche to bid managers, but—the Q&A period. It gives you the ability to influence and push: “Will you accept these additional materials?” They can show why our bid deserves to be shortlisted.

If not, you carve out space within the checklist exercise to push your offering as outstanding. Marketing brochures may have diminished, but there’s still a request for detailed information around the bidder—especially “describe your methodologies.” That’s open-ended. You can represent yourself strategically.

Even though AI evaluates it, that’s where it can ingest glossy materials and good copy and formulate it properly—if you use keywords, positioning, competitor understanding, market landscape, and buyer context.

Christina Carter (19:42) Oliver, what processes or rituals do you have to keep your bid team moving fast without burning out—especially considering they're working with multiple clients, multiple deadlines, multiple locations? It’s a tough job.

Oliver Streams (19:54) Yeah, absolutely. And the key thing is that they're working high volume, high stress, high pressure. It's short turnarounds and lots of work at any one time. So it's something I'm very conscious of—ways to motivate them and make sure burnout doesn't exist.

For me—and Elliot, feel free to disagree—communication and structure are very important. We're a small team. Right now there are four of us, with a fifth just joining. It's important to be defined in terms of who's responsible for what, and how we prioritize deliverables.

We’re a hybrid remote team, but we have open communication lines and regular meetings to make sure we're on the same page. I'm based out of London, the team is based in Stockholm, but we're on video calls pretty much every day. That close communication is key.

Building on that, it's critical to give team members ownership and responsibility over their work. There's no micromanagement. We're very flexible. It doesn't matter if you're clocking in at nine and leaving at five; what matters is the work. How you decide to do that—that's up to you. Ownership helps them feel in control of their work.

I like to run the overall comp plan as a commercial business. When the team is winning, the individuals are winning. Coming back to incentives: we're all aligned in the same way. Those times when there are multiple bids, it’s late in the evening, and you know you've got to get it out the next morning—you know the effort you're putting in will be rewarded.

In terms of setting it up as a sales organization, I see tenders and RFPs as part of the overall sales process, which hasn’t always been the vision of upper management. But for me it's important. From there, bid managers should be compensated similarly to salespeople. It's more difficult because you don't have control over closing the deals—but you do have control over volume and quality.

Christina Carter (22:24) Oliver, you know I've spoken about this before, and I’m obsessed with that idea. I wish everyone did that. I know so many proposal and bid team leaders who would love to do that as well. What would you suggest they do to get their leadership bought into this comp plan and way of working?

Oliver Streams (22:43) I think it’s important to convey to upper management the role that bids and RFPs actually play within a sales organization. If you can clearly demonstrate the financial output of the work, it becomes easier to get buy-in—if they can change their mindset and see it as a viable line of business growth alongside the sales team.

Once you get that buy-in, it's easier to structure the entire bid team as an extension of the commercial organization.

Another element is working closely with sales. There are crossovers. We see—not just in Tendium but across organizations—that RFPs often land with the salespeople. They're not professional bid writers. They're overwhelmed. By extension, the RFP team should sit close to sales. Then it makes sense that they're treated the same in terms of compensation.

Elliot (23:40) Yeah.

Christina Carter (23:50) Bid and proposal teams—they’re almost always burned out because it's deadline driven and there's a lot at stake. I never quite put together that maybe the incentives just aren't always there to help motivate you. Oliver, thank you. You've opened my eyes.

So to summarize—to help your team not get too burned out (although it's impossible to avoid completely): open communication, flexibility with timelines and hours, not having to sit in a chair nine to five, good compensation plans, incentives, and working closely with the sales team with the respect that sales teams get.

Did I miss anything?

Oliver Streams (24:43) I think the only thing I'd add—something we do at Tendium—is celebrating the wins of the proposal team company-wide, just like the wins of the sales team. It brings us even closer to the sales process and sales way of working.

In some organizations, bid and proposal teams disappear into the background. Celebrating wins and gaining respect across the organization is super important.

Christina Carter (25:14) So how do you do that? What does the celebration look like?

Oliver Streams (25:17) We have central communication channels where all commercial successes are shared. In that sense we're treated the same as sales—wins, contracts, successful bids are celebrated. In company-wide weekly meetings, successes are shared too. It’s about communicating to the wider organization.

Elliot (25:41) I’d add that we’re a relatively small organization that’s grown quickly. When I joined Tendium almost three years ago, we were much smaller. We’ve grown by over 200 percent. Three years ago it was easy to celebrate successes—you’d just stand up and talk to everyone in the office. Now it’s more formalized, but recognition still goes a long way.

Christina Carter (25:41) Very, very cool. Go ahead, Elliot.

Elliot (26:08) When I speak to our internal marketing team, they consider us a fundamental part of the commercial organization—not "those people who do bids; we’re not sure what they do." We're a central part of that commercial arm.

And I think it’s very important as a bid manager to be given agency—not being micromanaged in hours or in decision-making. I want to be the one to judge if a bid is a good fit or not. I don’t want to go to a manager to ask permission to disqualify a bid based on the relationship. I need to take those conversations directly with customers.

That delegation of agency and authority is instrumental because if I’m in control of how I work, I can dictate tempo. That prevents burnout and overburdening.

Christina Carter (27:17) Yeah, it’s almost like—as adults—we don’t want to be babysat. It’s something we’re good at, and yet that’s almost hard to find.

Elliot, this next question is for you. Is there a specific RFP habit or workflow that needs to disappear? And would you replace it with something else?

Elliot (27:20) Yeah. Yep.

The first one that comes to mind is an arbitrary word count or character limit for a response. I know that's dictated by the buyer, but it’s infuriating—especially when it’s a huge question. Recently I worked on a tender for a customer who offers AI functionality and tooling. The question was: “Explain your AI.” And I was given a limit of 150 characters.

What is that response going to provide the buyer? Ultimately, the buyer is better off allowing bid managers to use common sense. If a bid manager puts together a 20-page response to that one question, take that into account—you don’t need to accept it, but at least it’s meaningful. But 150 characters? What are you getting from that?

For internal workflows, it's less about killing habits and more about refreshing and revitalizing them—adopting new tools and processes. If we streamline and work leaner, we can increase volume and win rate. That's what I want. Internal habits are all part of the world we work in—they don’t need killing; they need refreshing. The things I'd eliminate are almost all format and buyer-related.

150 characters—try summarizing this podcast in 150 characters. It’s only a few words.

Christina Carter (29:49) Yeah, I think they want us to put War and Peace into a summary.

I'm also wondering—this is for both of you. You work at Tendium, which has tons of data. Is there a surprising stat or trend your data shows that contradicts how most teams operate?

Elliot (30:16) What the data shows me—and this is more a split between bid managers than a contradiction—is: I’m a big fan of extended qualitative responses versus simple yes/no. When we spend more time crafting a compelling response for each requirement, it often performs better than just ticking a box.

Understanding the target audience matters. That might not be the case if I’m working for a customer selling physical consulting services. They may not want that level of detail in an ESG questionnaire. But in software RFPs, qualitative context matters.

Another trend is buyers increasingly asking whether AI tooling has been used to write bids. My approach—and Oliver’s—is to treat this as an opportunity to demonstrate comprehension and strength in understanding AI, rather than something to hide. Especially in software—if you're selling AI-powered products, it makes sense to use AI to assist in writing the bid. But be clear and evidence your understanding and usage.

Gauge your buyer’s sophistication. If you're selling to a buyer with no understanding of AI, maybe they’re just afraid of it.

Christina Carter (32:34) Is that something you bring up during the Q&A with the buyer, just to gauge where they're at?

Elliot (32:41) Yeah. So if I identify this as part of an RFP in that first initial stakeholder meeting, it's one of the elements of my approach to the customer. I’ll ask: “How do you want to approach this? Do you want to go hard and say we're an AI-driven company with AI-powered solutions—this is how we use it, and this is how we've used our solution to answer your bid? Or do you want to say no AI has been used?”

You can also say something like: “We've only used AI for reviewing documents, but no text or formatting has been generated,” and so on. Then I give that to the customer to decide, based on how they feel the buyer will interpret it.

From my data, it’s becoming more prevalent in RFPs—especially in the EU, more in public sector than private, but growing in both.

Christina Carter (33:41) Yeah. I remember when I first saw that question—it was two years ago, and I didn't know how to respond because it was so new. I was like, “Am I going to get in trouble if I say yes? Will you get in trouble if I say no?”

But Oliver, I’m wondering what data you’ve seen from Tendium’s side.

Oliver Streams (34:01) I’d agree with Elliot about the questions around AI. Further to that, we've also seen questions like: “Have you engaged a bid writer to help produce this response?” If we work backward from that, buyers might be concerned they'll get ten responses to the RFP that are basically identical, just with the vendor names swapped.

I assume that’s their main concern—everyone using bid writers, and all those bid writers using AI. It’s an interesting trend. As you said, the first time we saw this was about two years ago. Prior to that, we’d never seen it, even though bid writers have existed for decades. So I don’t know if this is born out of bad experiences or fear.

Christina Carter (34:54) There was probably some procurement conference where they were told to ask that question—now it's in every RFP.

Oliver Streams (34:59) Yeah, I'm shocked.

Elliot (34:59) Okay. I mean, to build on that—I think I saw this argument on Stargazy or some bid-related space. The way people use AI is different. None of us use AI the same way. And if you have multiple bid managers working on a bid, that’s multiple personalities and work styles.

Using AI doesn’t create one uniform response. It creates multiple styles, just like having multiple bid managers. In FOIA requests, when I see actual submitted bids, I don’t see identical text. The fear is misunderstood.

If you compare it to schools where 35 essays on Pride and Prejudice are generated identically—that's not what happens in bidding. Bid writers aren’t prompting the same question in the same way for identical text. The fear is misplaced and shows a misunderstanding of how bid managers work and how these tools support us.

Christina Carter (36:29) Yeah, I agree. If teams use AI poorly, the response will show it. But before AI, if someone didn’t know how to respond well, they produced a poor response anyway—it just had worse grammar. To me, it’s not that big of a worry.

Well, it was lovely to chat with both of you. And if anyone wants to ask Elliot or Oliver questions about their experience—especially on these topics—there will be an AMA with them in the community. Just go speak with them there.

It was lovely to talk with you both. Speak soon.