How to Win RFPs in B2B Enterprise ✹ Kristina Nolan (HubSpot)

Christina Carter: Hey Stargazers, today we're speaking with Kristina Nolan and she brings a wonderfully broad leadership lens to proposal strategy. She is a Proposal Strategy Manager at HubSpot, and she's been a proposal manager at SchooLinks. But she has built her career being a VP of Operations. She's worked in finance, she's worked in revenue execution. Her background spans high growth leadership, business operations, and client-facing strategy, which gives her an interesting and exciting view of proposals as serious commercial discipline. Whether you are a revenue leader or you manage a full team of proposal people, this conversation is for you. Take a listen. I'll see you on the other side.

Christina Carter: Hey Kristina, thank you so much for joining the stargazy Brief.

Kristina Nolan: Hey, thanks so much for having me.

Christina Carter: For the people who don't already know you, you have a really long background in both proposals and operations. A lot of people we interview on this podcast have a proposal tech background, whereas you are a proposal practitioner, a proposal leader, operations leader within tech. One of my biggest questions for you is: what does an RFP reveal about a buyer that a sales call can hide?

Kristina Nolan: That's a great question. It's something that is on my mind every time we receive an RFP. There are certain things about a buyer's intention that you can glean from an RFP. On my team we're always looking at whether requirements mirror ours or our competitors. That's of course a surefire way to identify who maybe shaped this, who maybe spoke to the buyer already. That can come through in the RFP. I've also noticed specific phrasing and terminology, the way that the solution is written about, can often signal whether a decision has either already been made or whether it's a true fair evaluation process. Ultimately you have to know how to read between the lines for your industry and for your vertical to understand your competitors and to look for those signals in an RFP.

Christina Carter: It's so easy when you've spoken to a salesperson, an AE, and they get on that call with you and they say, yeah, they were so nice, they're so good, they love us, we're definitely at the top. Then you get the RFP and it's like you said, that has that competitor language. Let's say I'm joining a new team or a new company and maybe I don't know what those competitor keywords are. What would you suggest I do to upskill myself or uplevel myself to being able to read an RFP and saying this isn't for us, this is for somebody else?

Kristina Nolan: As part of your onboarding, I would hope that your onboarding includes at least a little bit of a description of the landscape that you're in, who are your biggest competitors. I would familiarize myself with that as much as possible. You can do a little bit of research there on your own. ChatGPT is obviously a great place to start to get some of the basics, and then you can dive deeper on your own. In tech, we all know who our biggest competitors are, at least in SaaS. It's pretty obvious. It's something that can help you out the gate, not just identifying maybe where some biases lie, but also where you have an opportunity to differentiate yourself.

Christina Carter: Do you ever use technology to try and figure that out? Do you rely on software to help you with that?

Kristina Nolan: It's a bit of both. Being in tech, my SMEs are our solutions engineers. They're often my biggest resource when it comes to this. We have folks who within just a few seconds of reading it know the terminology, and they've been in the game long enough to understand, this sounds like this, and identify those things right away. We use technology for that too. We have built our own agents with our internal resources to help us identify that in an RFP as well.

Christina Carter: How do you know if you're a true competitor for a deal within an RFP, as opposed to just being that fourth, fifth person who needs to be there for procurement to take a box? What else is in there other than just the keyword red flags?

Kristina Nolan: From my perspective, it boils down to the relationship and the engagement with the buyer throughout the process. I'm so glad you brought up just now that sometimes you'll get on with a sales rep who says, yeah, we just met with them, they're so excited, they were so nice to us, they love us. It's so important. If I could ask sales folks to remember one thing when getting into an RFP, it's that it's their job to make you feel special. It's their job to make you feel like you're the only one that they're considering. Otherwise, why would you give them the time of day? Why would you give them all this attention and information?

The majority of the work we do is in the private sector. Serious buyers will engage with vendors even after they've released the RFP. They are willing to answer questions, be it via email or hop on a quick call or connect you to the right person to answer some more technical questions that they can't answer. They want to make the right decision and so they're willing to hear what you have to say and answer your questions.

Christina Carter: How are you going to know that necessarily? Sometimes you don't really need to talk to them during the RFP. You know them, their requirements are strangely clear, you know what's going on. How would you test that once you do receive an RFP if you don't need that conversation?

Kristina Nolan: That is why we always take advantage of a Q&A if it's provided. If they are allowing for vendors to send in questions, even if we think we know everything, we ask questions that dig at the intention a bit more. I ask, who else are you evaluating? How many other vendors are you evaluating? Buyers don't always want to answer those questions and they don't always answer those questions. But if somebody tells you, we're looking at three, you're one of three vendors that we're looking at, at least in SaaS in my world, to me that signals this is a pretty targeted evaluation. You've already done your research and you've narrowed it down. If it's six, seven, eight plus vendors, that to me is more of, we don't really know what we're doing and we're throwing spaghetti at the wall and hoping something sticks.

Christina Carter: Is that then part of your qualification process when you're sitting down with sales leaders? Have we already engaged with the buyer? Will they continue to engage with us? Is there anything else that you tend to, I know this is a generalization, but for the most part should be in everybody's qualification scoring matrix or whatever it is that they use?

Kristina Nolan: Absolutely. That's part of it. It becomes even more important if there's any sense that from a technical standpoint, you're not actually going to solve for everything for the customer. It's not written in a way that you're like, yep, we can do all of these things, check the box. That's when it becomes even more important to understand, do they really know what they're trying to buy? If we can't satisfy all the requirements, does the buyer understand that? Are they willing? Do they know that this might be a two-vendor solution? That becomes important when we're talking about digital transformation projects and things like that.

Christina Carter: Is there anything else you think is useful for most people in terms of qualification?

Kristina Nolan: Those are my big ones. There are some other indicators of the savviness of a buyer. In tech, we're often working with partners that are delivering and implementing and integrating the solution. A willingness to evaluate and ask for an implementation plan signals a true, okay, you've thought about this and you know what this process looks like. I always get a bit scared when there's no mention of that in an RFP. Have you thought about this? Not only is it going to be an investment of your time, but also money to get this off the ground. That's an extra cost.

Christina Carter: It just magically starts working in your environment.

Kristina Nolan: Yeah. Depending on the needs, it's going to come from an implementation partner. If you're not asking about that in an RFP for a SaaS solution, that gives me pause. To me that signals, well, maybe you've already figured that out and that's why you're not asking, or you're really not a savvy buyer and you don't know that you need to ask about that now.

Christina Carter: Qualification is so important to our win rates, which proposal people care about, but usually CROs aren't measuring those win rates. What are you seeing CROs measure that's wrong, and what are they measuring that's right when they're looking at RFP performance?

Kristina Nolan: Proposal professionals are always thinking about win rate. From a CRO perspective, I'm fortunate that win rate is a consideration, but at the end of the day, it's the bottom line. It's the revenue generated. That's the driving factor. If you are in a position where you're seen as an extension of a sales motion, or you specialize in a particular kind of sales motion, you are likely going to be evaluated like sales reps and sales folks. What they're not measuring though is how many RFPs did you disqualify yourself from, or what we say no-go essentially. What they're missing out on, and what a no-go rate really does reflect, is your strategic focus, your good resource stewardship, and your qualification rigor.

Christina Carter: Do you think there are any things proposal and bid people should be speaking about when they are speaking to revenue leaders?

Kristina Nolan: I really think it's important for proposal folks to have a strong and rigorous no-go process and standard so that they can show revenue leadership teams the opportunity cost of going after and chasing deals that are a low likelihood of being closed-won. My leadership cares a lot about that. They don't want to see sales reps chasing stuff that they would consider a distraction. I often have to be the bad guy in the room to bring up the risk to a deal.

Another thing we care a lot about as proposal professionals is our shortlist rate. I can count, in the two and a half years I've been with HubSpot, on one hand, the number of times we haven't been shortlisted or proceeded on to a demo stage. We almost always do, not because I'm so great or my team is so awesome, but because of the nature of how well we qualify, and because we make sure we're competing in rooms where we're going toe to toe with folks that it makes sense for us to go toe to toe with.

The time spent on a proposal is not the opportunity cost. The opportunity cost comes when you've got an SE, a salesperson, a partner, and you bring in your legal resources, your deal desk resources, and whoever else to go along this process that might involve multiple demos, on-site visits, and so on. It's not just time either. It's cold hard cash that you're spending on these sales processes. If you can identify early on that there's a huge risk and try to dig at the root and find out if it's a true risk, you can avoid altogether.

Christina Carter: Where do you see in the proposal process where you're losing before you even receive the RFP?

Kristina Nolan: We have such a large partner ecosystem and a lot of those partners of ours act as consultants. They will recommend HubSpot to customers. If it's not one of those, it's really easy to find out. All you have to do is go to the consultants' website and look at their case studies, or look at who they're putting down as references and what kind of solution they recommended to that reference. That gives you your answer. If you've never seen your company's name, if I look at a consultancy and I never see HubSpot's name on their site, that's a pretty clear signal.

Christina Carter: When AI makes every proposal sound so polished, what makes the ones that you write feel more trustworthy compared to all those more polished AI-generated ones?

Kristina Nolan: AI is great at delivering a polished sounding and looking proposal. We always talk about compliant and compelling proposals. In speaking that language, I feel like AI can normally get you 80% compliant, but only 30% compelling, at least from my view. What stands out then and what makes proposals in an AI world sound authentic is to speak to customer-specific insights and details that you've gathered, either because you've had a relationship that's been building or you are demonstrating that you've done your research and you know their pains, you know their industry, and you know what kind of solution will best benefit them. AI can help you with that a bit, but it's hard to write a proposal that's truly going to speak to a customer's needs the way that we can with just AI.

Christina Carter: Is your suggestion for proposal teams to have AI generate that first draft, and then you take all the customer insights you have and add them into that draft response?

Kristina Nolan: We use AI to draft. We even feed AI the customer insights and ask it to consider that when drafting. What you can do, and what successful proposal teams are doing, is they ensure that whatever agent you're using is using your authentic brand voice and that you can take a pass to make it sound like a human and not a content generator. That will go a long way. When I said AI can get you to be 80% compliant, it does make mistakes. It'll say things that aren't necessarily true. I've had AI insert references into proposals that don't exist. Names, phone numbers, those aren't real people, those aren't real references of ours. While AI can do a wonderful job at giving you a polished proposal, it's not going to give you that persuasive, compelling, insightful delivery and language that we are used to generating for our proposals.

Christina Carter: Are you taking a second pass with those customer insights and adding them in to make sure that it's even more customer-insight-heavy and compelling?

Kristina Nolan: What we try to do a lot of is, especially in our executive summary, we have the whole deal team — a sales rep plus the solutions engineer plus our partner — take a look at the language we're using there and verify, this really does sound like what it's like when we talk to our customer. That's a part of our proposal that gets an extra couple of sets of eyes on it. Then throughout, wherever we are referencing the solution we're proposing, making sure that we're not saying, this product is going to accomplish XYZ for you and give you 1, 2, 3 features. We make sure we tie that to: it's also solving for these specific gaps in your current processes and systems that you mentioned when we spoke to you, or in the RFP in this section. We tie it back to what the customer has given us.

Christina Carter: You're unique in that you have a strong operations background. Is there something you're seeing that proposal people, salespeople should be doing differently?

Kristina Nolan: It's important for sales folks and proposal folks to always consider our audiences. What I always remind my deal teams about is that this proposal is not only going to go to your point of contact. This proposal is likely going to get passed around to a bunch of people that have never spoken to you, and they may all have a hand to raise when it comes to the final decision. We have to make sure that whatever we're putting on paper is reflective enough and compelling enough of what solution we're trying to deliver for them. Considering those other personas, especially from a procurement standpoint, is where sales folks could stand to consider a bit more.

Christina Carter: Are there any best practices that you're using that are working really well that you've never been taught?

Kristina Nolan: Where my mind is a lot lately is in AI. We at HubSpot focus on it tremendously. There's a huge push and encouragement to not just use the AI tools that are available to us, but to truly explore and play and figure out different ways to use it to take away some of that repetitive manual work, but also to unlock more imaginative and bigger picture thinking work that can get done either with AI or without, but to free up space for that.

Christina Carter: Is there anything specific you would suggest? Hey, proposal people, go play with this now.

Kristina Nolan: There are a lot of really cool things you can do with agents, depending on the kind of tools you have available. I sit in a privileged position in tech where I don't have a shortage of AI tools to play around with. I would highly encourage people to learn as much as possible about how they can build even simple agents within some of these tools that can streamline and simplify all of those manual tasks you do every time you receive an RFP.

Christina Carter: Whether it's AI or not AI, what should a CRO do personally in an RFP motion or proposal process, and what should they stop doing that you keep seeing them doing?

Kristina Nolan: I love this question because thankfully I have great revenue leadership. We have a Chief Sales Officer who is fantastic, and really all the sales leadership that I work with and teams that I support are able to lean into these processes. Something I see that works really well from sales leadership is executive sponsorship on RFP deals. That is something that I try, from a strategic guidance standpoint, to encourage on certain deals. Try to title-match, whether it's with a sales leader or somebody else within the company that matches up with the buyer's leadership that's also looking at the solution you're proposing. If you can get that executive outreach going early, that's something that our sales leadership does that's effective. Not only is it effective for the deal, it's showing the buyer, we're engaged, we care, we're getting leadership involved here. Your deal teams feel super supported when that happens. Every step you take, higher up is going to see that you're taking these steps. RFPs can feel so behind a curtain. Deal teams just feel really supported when they get involved like that as well.

I have the benefit of a lot of trust and support from that leadership. The more that CROs can trust their proposal professionals to really quarterback these deals, to direct traffic when it comes to the cross-functional work, there is a ton of cross-functional work that goes into proposals. Just having that trust is huge. If I could say one thing, I would say, please resource your proposal teams appropriately.

Christina Carter: Where do you tend to start that executive sponsorship within the proposal process?

Kristina Nolan: It depends on the deal. It depends how it came to us and at what stage I'm getting involved. If I'm brought in really early on a deal, before we even receive an RFP, we've spoken a lot with the buyer, we've influenced the RFP that's coming out, they want to buy HubSpot but they've got to go through the proposal process, that's when I would get somebody involved even at that stage. Especially if we don't feel like we have enough visibility into all the different folks who are going to be making the decision. If we've been a bit too single-threaded in the conversation, that's a good place to start early.

There are times where we get to post-demo and all of a sudden there was a CTO on the call that had a lot of challenging security questions, for example. That's when it's like, this makes sense for us to bring in somebody from our security leadership team to make sure that we're showing them that we care, we saw and we recognize the questions or concerns, and we're responding to that appropriately.

Christina Carter: Are you having them take part in the proposal response at all or the review?

Kristina Nolan: The executive sponsorship doesn't really come into the proposal itself, although occasionally we'll have them deliver a note alongside a proposal or something like that. That can go a long way. It's important to work with the deal team to understand what kind of title-matching would be best, who in their networks. We leverage LinkedIn to see who from our leadership might know somebody in their leadership, and what makes the most sense. What events do we have going on? So-and-so is going to be at this event. Let's invite them to come to our event next month. Things like that. If we can coordinate, they can serve us really well.

Christina Carter: What would you suggest proposal people do so that the revenue leader does trust them and want to resource them?

Kristina Nolan: That's a great question. It is an unfortunate reality for a lot of our colleagues. In those cases, data is king. Come with your numbers. Make sure that you track the wins, make sure that you track where you have no-go'd to and saved the company time and money. All of those things are things revenue leaders care a lot about. They care about the bottom line. They want to know how much revenue you generated, but they also care about time, opportunity cost. If you can show that you're saving there, that's huge.

We didn't really talk a lot about capture here, because in tech and in the private sector especially, capture management is not the same as it is in other industries. Proposal folks are seen more on the playing-defense side when it comes to RFPs. The more we can show that we have value to add on the offensive or on the more prospecting side of things — where we can help sales teams identify industries and verticals and segments that rely on RFPs for purchasing, and that we can help anticipate that and guide the strategy there — that's a huge unlock for proposal folks.

Christina Carter: Are you also including proactive proposals in that early-stage offensive approach?

Kristina Nolan: Prescriptive, like writing a proposal for a potential buyer who hasn't gone out to RFP. Absolutely. I don't think it's a secret that people do that. Now some of the really big value from AI is that we are no longer just sitting on a template that we email out to everybody who says they want an RFP template. We are generating bespoke, custom, tailored RFPs for anybody who even whispers that they're going to need an RFP. That's a way to leverage AI for sure, if I could recommend that folks do that.

Christina Carter: Where can we find you?

Kristina Nolan: I'm on LinkedIn. I'm more of a lurker than a poster, but I love to connect with people and chat. I am in the PIE network. I love connecting with folks there.

Christina Carter: Thank you so, so much. This was absolutely wonderful and very insightful.

Kristina Nolan: Thanks so much for having me. I loved it.

Christina Carter: I hope you enjoyed that conversation with Kristina Nolan. She is so insightful and has so many great ideas for things that proposal and revenue leaders should be taking into account when responding to and winning RFPs. If this helped you at all, please like, subscribe, and share this with a proposal or revenue leader friend so they can also learn how to win RFPs. I'll see you next week.