🎤 You down with RFP? Yea, you know me!
Nolan re-lives a $500k enterprise deal. Starting with a few teams & grew to hundreds of users.
After literally writing the Request For Proposal (RFP) for them, running discovery meetings with 15 decision-makers, & hosting a 3-day on-site demo; he still almost lost the deal due to a brand new executive trying to make their mark.
How did he save it? Well...you'll have to listen to the episode:
Guest Feature
Nolan jumped from teaching assistant to sales rep in 2011 & has skyrocketed from there.
Promotion after promotion, he’s climbed the Account Executive ladder and specializes in closing large enterprise deals.

What problem does Adobe solve?
Adobe is massive. Nolan forces on the work management space.
Helping companies with digital review, approval of assets, the end-to-end lifecycle of work.
Adobe offers an operational system of record or really a single source of truth for their work.
Deal details
What are you selling?
- Software to streamline review & approval processes in an enterprise org.
Where did the prospect come from?
- They were on Nolan’s target account list.
- Previously a closed-lost two years prior.
Company type
- Global media company. 100k employees.
Prospecting method
- Worked closely with his sales development rep. Targeted cadence email to several teams. Prospect went to website & requested a trial.
- Land & expand method. Started with a team of 50, expanded to around 400.
Barriers to Overcome
- Prospect hired a new CTO mid-sales cycle who brought a semi-competitor on their own.
Buyer type
- Decision Maker: ~15 directors of teams
- End users: ~15 teams. Art, Media, Technology, Marketing, Technology, etc.
Episode Highlights
Note: timestamps correlate with the full conversation
Prospecting: Cadencing 15 decision-makers at 1 company (5:39)
Discovery: Creating the RFP process with your prospect (12:16)
Demo: The magic of the on-site demo experience (19:18)
3 Tips for Account Executives
1. There's no magic bullet to meeting quota.
Just consistency over time & a lot of elbow grease.
2. Be more like a consultant, less like a salesperson.
Help them uncover solutions, not just problems.
3. Rely on your internal ecosystem.
No matter the size, every company has resources you can use.
Watch the full conversation
Full transcript
Taylor Dahlem
Welcome back to How I Deal! where we discuss past close one and lost deals, how they ended up that way, and provide some real tips for account executive and other full cycle sellers to use in their deals today. My name is Taylor Dahlem, full-cycle account executive turned content guy, and as always joined by my superhero partner in crime, Junior Lartey. How is it going man?
Junior Lartey
Really solid. It's episode nine since passing the death date of all podcasts. I'm like wondering if this is just my life now. Like am I going to be sixty running this How I Deal podcast? It's probably too early to think about that, honestly, but that's what I got for you today.
Taylor Dahlem
Yes, just like startup life at the end of the day, every day we're fighting for our next day, but love to have our ninth episode here. Things are moving quick. A quick refresher each conversation. We want to chat through a past deal, but keep all names, places, fictionalized anonymized because that'll help us dive deeper the first time this individual saw the prospect or ultimately they led to the demo, the discovery, all those things. How did they get to that point? From point A to point B, we want to dive deep.
Junior Lartey
So today we've got a good friend of mine, Nolan Hansen. He's an account executive formerly at Workfront, now Adobe due to acquisition. I feel like talking about an acquisition like that could be a podcast by itself, especially in selling like, hey, now I'm selling two things at once, but we're going to try to do a really good job to tie those things together. Nolan, thanks for joining.
Nolan Hansen
Great, thanks for having me. Happy to be here as well.
Junior Lartey
Awesome. Nolan, give us some insight into your role and what problems Workfront in Adobe solves.
Nolan Hansen
Yeah, I appreciate that. So Adobe is obviously a super large organization. They have over forty products that they sell and offer to customers. Specifically my area of focus within the work management space along with digital review and approval of assets and really the end-to-end life cycle of work. So as an organization, what we do is with our platform, we offer our customers an operational system of record or really a single source of truth for their work.
Taylor Dahlem
Awesome, well we appreciate that rundown. Nolan, let's dive right in. What deal are you walking us through today?
Nolan Hansen
Yeah, so the deal that I wanted to share today is a well-known global media company. Along with its streaming service, this organization has nearly one hundred thousand employees. They're, like I said, well-known throughout the media and entertainment industry. And this opportunity started out smaller and ended up growing to hundreds and hundreds of users, the contract being just shy of half a million dollars. So it was an exciting one from start to finish.
Taylor Dahlem
Massive deal. Massive deal. I think we've had a run of enterprise deals over the past couple of episodes, but this one by far, I think has the most twists and turns and we're excited to dive in, so let's do that. In the past, reps learn about a company, maybe through a target account list or from the CRM on LinkedIn, word of mouth even. How did you in particular find out about this company and maybe what was the extent of the research that you did to learn more about them?
Nolan Hansen
Yeah, this account was on my target list. This was kind of starting out in two thousand and nineteen, by the way. So it was previously a closed loss opportunity from two thousand and seventeen, meaning they had evaluated our system two years prior. So my DSR, my digital sales representative, my counterpart, and I saw that this was on the list, that they had a close loss opportunity and that many, if not all of their competitors were already customers of ours. That was something that we really wanted to kind of dive into because we already played well with a lot of their competitors.
Junior Lartey
I think that's a huge aspect is the fact that in this space, obviously all the companies are really well known. This is the last of the big fish that is not with you. So it would be really easy to just and we've said this in the past, like, don't sleep on inbound, but it would not sleeping on reputation and just like, hey, we're Adobe, we're going to win this deal. But really allowing the sales process to take place is something that we pre-chatted, obviously, but something I think people will recognize. Just like, don't sleep on your reputation, don't sleep on who you are. Because this was previously closed loss, meaning that in the past, you've lost this deal before, so now you got to find a way to get in front of this prospect, which sometimes is easy, sometimes it's not. Give us some details on that experience.
Nolan Hansen
Yeah, I definitely want to give full credit to my DSR. As mentioned, we work together. Seeing that this account was one that we wanted to get into, that we wanted to target, we put together some targeted messaging specifically to the director level that seems to be a good fit for the type of sales cycle that we run. And so we sent out targeted messaging to anywhere between fifteen to twenty different directors, ranging from Director of Art, director of Media, director of Technology, to marketing Director. And looking back on it, eventually, one of those people who originally had received several messages in the cadence went on our website and submitted a request for a trial. And that's kind of how we were able to engage with them head on.
Junior Lartey
So we're talking about cadencing fifteen people from one company, right. Typically it's like there's maybe one or two decision makers. You're going out and you're essentially like recruiting a whole army here. Were there any hesitations that one director might be like, hey, no, thanks. We already use X because you're still reaching out to others. So what's the play there? If one does respond and they're just like pass, but another response and says yes, and now you got like conflicting people, I don't know, talk us through, like is there a fear in doing that?
Nolan Hansen
Yeah, I think there's definitely pros and cons to that, as well as the fear that one of them is going to shut it down. But I think that's also the benefit of multi threading and not just kind of putting all your eggs in one basket with one director. Right. You could get very specific with one person, but by kind of spreading that out a little bit, I think that's where you use numbers to your advantage. I know we wanted to refrain from just the typical spray and prey method, right. So we weren't messaging thousands of their employees. That's not what we wanted to do. It was specifically messaging targeted for director level. And that's kind of why we reached out to those directors across the board.
Junior Lartey
I think that's probably the big difference there is you've got fifteen that you've selected and it is targeted messaging as compared to spring out like you mentioned to the fifteen, just like something canned that now they all can say no to. That'd be pretty rough. And I thought I knew all the terms out there, but DSR, I'm just going to go ahead and assume that's like the equivalent of an SDR or a BDR, am I correct in that assumption?
Nolan Hansen
Yeah, exactly. I think at the time they were even called Adm. We've changed multiple times. We've gone from SDR, BDR, ADM, DSR.
Junior Lartey
Okay.
Nolan Hansen
Probably another acronym coming up soon.
Junior Lartey
Yeah, Account Development Manager is ADM. Right. So we'll try to catch all of those as they come.
Taylor Dahlem
Yeah, we're used to the alphabet soup world of sales, but it always helps listeners out there what exactly the teamwork look like and the structure of the organization. But Nolan, a lot of moving pieces here. Like, you all were talking about fifteen or so decision makers or at least people that are involved in this deal that you've looped in and you've specifically spoke to whatever pain, whatever goal, whatever thing that buying trigger that gets them to move. Once that happens, prospecting-wise, the next step is usually that initial conversation, and in my opinion, and probably most would agree, the most important piece of this entire sales cycle, which is the discovery conversations. And in this case it sounds like it has a ton of potential to be a mess just in the sense of how many people are involved. What did that look like, those initial conversations? How did you keep it all organized and straight for your side of the table and what did you learn?
Nolan Hansen
Yeah, a lot of good points to cover there. So we started out with the one director and the funny thing with our system is it tends to be contagious. So different teams, when they see other people either trialing out the software or having demos, those types of conversations, they want to be involved as well. Before we even got to any sort of demo discovery phase, really grew from looking at one or two teams to multiple teams. And we ended up doing over ten Discovery sessions. Some of them were follow ups and some of them were unique teams because there were so many groups involved. But I would say the advantage that we had throughout the process was focusing on them. So I've learned and I've done it in the past, made the mistakes during Discovery where it really becomes an interrogation. And that's not what we wanted to do. We wanted to make the Discovery really about them and how we could uncover challenges that they didn't even know that they had, as well as look for ways to gain efficiencies throughout their process. And so by the end of the ten plus Discovery sessions that we had with them, they really viewed us as their partners, as their business advisors. And I think taking that consultative approach really helped us gain that advantage.
Junior Lartey
Talk to us also about the RFP at this point, because a Director that you had previously reached out to came inbound after going inbound, you reach out to them, you schedule meetings and then, as you mentioned, contagious, right? So this thing really starts to grow. And ultimately you had mentioned very early on this deal grew from just fifty to four hundred users. So obviously there's a lot of things that are contagious about workflow, about Adobe, what you're doing over there. But the Director introduces the thing, but then it turns into an RFP situation, which can be quite the task. Right? Because usually an RFP, which is Request for Proposal, usually that means we're reaching out to you and everyone that you play ball with. Right? So talk us through that RFP situation. Not fun and not ideal.
Nolan Hansen
Yeah, so the RFP definitely adds time cycle. I don't think I've ever worked a single deal where an RFP has streamlined the sales cycle. It again does quite the opposite and always adds time. And so they let us know initially as we were going through Discovery calls and Discovery sessions with them, that per their policy, they would have to issue an RFP. Where I think we again had the advantage was because we took that consultative approach, because they viewed us as the experts. And we again name-dropped really all of their competitors who also use us and how they had success in different scenarios. We helped write their RFP. So our internal RFP team helped create questions that were geared really towards our software and what we offer. And while it still was a process, we still had to go through the RFP, we still had to answer the questions. Many of the questions were questions that we had submitted for them to include in their RFP. So in the end we ended up obviously winning that RFP as well.
Junior Lartey
I think that's huge at this point. You have become advisors, you become more than friends, right? You're in on this mutual goal to find them the best solution and being able to influence what the RFP looks like and the things they need to be concerned about is huge. Really huge. So I'm trying to think, okay, I'm in SAS, maybe I'm not selling a half a million dollar contract, maybe nobody really does RFP. But here's what will happen in almost everybody's deal. You'll approach someone, they'll have interests, they'll take a Discovery meeting with you and then they're going to go and do research and they're going to look up all your competitors and likely they will book meetings with people that you play ball against, right? So what you can do in your Discovery is take a similar approach where if you know after this conversation, they've got to go look at your competitors, position certain things so that when they do go look at competitors, it's not that you are lying, it's not that you are trying to pull the rug from underneath them, but you're helping them take a different approach to which speaks, I mean better to you honestly, right? That's like the salesmanship, the tact of the actual sell. So there's your comparison. You might not be getting RFPs, but if you are introducing a conversation, I can guarantee you they're doing research and reaching out to other people. So post Discovery, it's demo time. You got to show the product walking through different workflows, anything unique through this demo experience.
Nolan Hansen
Because there were so many groups involved, we offered to do an onsite demo. We like to call them Working Sessions as well. So not just a demo of here's the product, but actually work with them. So I think it's what we had them titled as On Site Working Sessions and it ended up being a three day on site with them at their headquarters. Full day, like eight to five working sessions with a break for lunch, obviously. But it provided a ton of value not only for us, but for them as well. During these working sessions and demos, they were uncovering more problems that they didn't even know that they had. We were understanding their business even more than what we thought we knew. And that seemed to be something that happened each time we met with a new team or a different group as we were understanding them more and more, which I think again goes back to taking that consultative approach and really becoming their business advisor. And so in those working sessions, they asked for the recordings, they asked for the recordings of all of the demos, really because they wanted to take that back to their own strategy team and look at their own internal processes as they had uncovered different challenges and different areas where they realized they could improve on as well.
Junior Lartey
Okay, I've got two follow-up questions to this because I think this is really important to understand. One is, did your competitors do this as well?
Nolan Hansen
They did not, because we had already and maybe they offered, I'm not sure, but by the time we did the onsite working sessions and demos, we had already won the RFP, so they were only having us come on site. At that point, they weren't even considering anyone else, which also is in a really good position to be in, right?
Junior Lartey
Yes. Okay. So this could be, as you're working with the champion, they could say, Hey, we're leaning towards working with you. This is when you as a salesperson, really step in and try to take over the conversation and make it, we're leaning you, and the only decision and option is you. So to make a different demo experience, maybe you can't do three days on-site, but you've got to do something different than your competitors, which your competitors are going to do. So my other follow-up question is simply like, how do you get a customer to commit to three days of on-site?
Nolan Hansen
Now, looking back on this, I want to say it was them that actually requested that much time, because typically we don't do that. We'll do maybe a full day of three demos or something like that if it's a larger deal, but usually we don't do several days in a row like that. So this was a little unique. Again, if I'm remembering correctly, I want to say that they were the ones that had requested that on-site, and it worked to our advantage as well as theirs. And back to your point, Junior. For those that maybe aren't doing even on-site demos or visits with their customers, I think there's something to be said about educating your customers, your prospects.
Junior Lartey
Right.
Nolan Hansen
Whether it's a small sales cycle or a large sales cycle, you can still educate your prospects and really help them understand from your point of view as well as you're the expert in your field. Right. So each of you who are listening, you know your product, you know it well, you know how it's going to benefit them. So I think educating them is really a big part of that, and it's super important.
Junior Lartey
Okay, here's a different question.
Nolan Hansen
Yeah.
Junior Lartey
Talk about the magic of what happens when you go on site.
Nolan Hansen
Yeah, going on-site is one of my favorite parts of this role, and I'm glad that we have the flexibility to go on-site with customers as well as prospects, but meeting them in person really creates that relationship. It really creates that partnership. I remember walking into their headquarters, and our main champion, she runs up to us and hugs myself and my sales engineer, we've had obviously many sections with them, but even then, from that moment forward, it's like, okay, this is going to be a good time, right? Things are going to go well. They're excited for us to be here and they had a room set aside for us. They were really excited for us to come in and really kind of be those business advisors as we're presenting offerings to them that can help with some other challenges, their pains that they're experiencing. This particular example, I think the only customer that I've had such a good relationship, this is, I would say the only customer that I've added on Facebook. Sometimes they'll add us on there and usually I'm like, I don't know, I'll keep personal life and business separate. But we added them because they were so great to work with and they really viewed us as partners.
Junior Lartey
People really put their guard down. When you can get them on-site, you're learning a lot more there. I love that experience and what it was able to do for you.
Taylor Dahlem
Nolan. So let's just plow ahead to the next steps.
Junior Lartey
Right?
Taylor Dahlem
So typically after ten-plus discoveries, like you were talking about three-day on-site demos, you hope it goes well or perfectly according to plan, but as we know, nothing in sales ever happens exactly how you think it will, which is what makes it interesting, which makes it as much an art as it is a science. So what barriers or what objections maybe came up throughout that process that you had to overcome?
Junior Lartey
Yeah.
Nolan Hansen
So Taylor, you mentioned talking about closed lost and closed one opportunities. This is both of those. So we ran into a big roof block during that on-site time. This was in March of two thousand and twenty. So right before kind of the Covid shutdown, which we thought would hinder us, but actually helped because of their business of streaming and their business of media, entertainment, movies, everyone was home watching movies and streaming. So that wasn't the roadblock. But the roadblock was that they got a new CTO and a few months later, as literally within a week and a half of them that they were going to sign the new CTO, bought a semi-competitor, went behind everyone's backs, ours as well as their own internal employees, and bought a semi-competitor. And it was a very emotional day when they let us know that they could not move forward with us after spending a year and a half in that evaluation phase and spending so much time together. They were distraught, we were distraught, and it was definitely a mess.
Taylor Dahlem
Yeah. I would say that doesn't feel great at the end of the day when that much work is put into and then all of a sudden, I guess my question is there any background given to this individual, this much work has been put in, or what was the communication like that led to this happening?
Nolan Hansen
Yeah, so they shared with us that they had begged and pleaded and shared how much work they put into this, to the point that my champion had to take two days off from work. She cried on the call. Her VP was emotional as well on the call. And when they let us know that their CTO had purchased something entirely different and it was already said and done, he had already made the purchase behind their backs. Again, I'll just say this was the only deal where in eight years I've been here that I actually cried as well. I held back my Tuesday in the call, but shortly thereafter it was that devastating to all of us because we were all completely blindsided. And looking back, obviously, when they got a new CTO that should have been an area where we dug deeper, I think I probably was like, oh, does he know we're talking? And is that okay? And they probably said yes, but really should have spent more time there. So looking back, that's an area of improvement for sure.
Junior Lartey
Einstein is also so hard because as you mentioned, looking back, okay, new CTO, what does that mean? And you could take that a lot of different directions, probably spend some individual time with them, try to understand them better, try to get their mindset right and see like, you're stepping into this organization, what are you going to do? In this case, they bought a semi-competitor, and this podcast was meant for closed one and closed lost deals. We weren't expecting to get to the close loss aspect so soon. That's like episode ten kind of stuff, right? But ultimately we know that this deal kind of comes back around. So what happens from here?
Nolan Hansen
Yeah, so we closed it out. My VP had gotten on trying to save it. Our EVP had gotten on as well, and there was really nothing that we could do. We closed it out. We knew that they would likely come back to us, mostly because they had purchased a semi-competitor. Having known their challenges, knowing their issues, when we heard who they had purchased, it didn't make sense to us. And we were like, that's not going to solve what they're trying to solve. That's something completely different. And so fast forward ten months later. We're now in two thousand and twenty-one. Again, this started in two thousand and nineteen. The SVP of Technology called me while we were out of the country. We're on vacation actually, my wife and I, and he called and essentially said, we're ready to move forward now. And their CTO had been let go. So they didn't have that roadblock internally, and they were able to move forward within a month.
Junior Lartey
So now you're fast, it's like, okay, two years worth of conversations and then ten months of dead quiet. And then when they reach back out, it's like all the value that you built over two years, it's not like it just dissipated. It wasn't gone right. All that velocity. They still remembered the onsite, they still remembered the value of the tool, the product. So I guess the final question I would ask is you get that phone call. Did you cry again? Because now you've won and you're on vacation.
Nolan Hansen
No, it was super exciting. And I think to your point, Junior, all the work that we had done, the value that we had provided was really kind of banked there, it was stored there. So it really helps streamline four or five weeks close, right, within a month period. And they were running against timelines because they had a system that was depreciating and so that worked to our advantage that they basically said, hey, we're ready to move forward now. We don't have these roadblocks and we need to get this done ASAP. And of course we were excited about that as well.
Junior Lartey
You're just controlling what you can control, right? Like doing your absolute best in all your respective areas and know that once you've done your best, you've played your card. I don't know, you have to have understanding around that. And in this case it was a semi-competitor and poor decision from someone that came around and met them in the butt. But you controlled what you could and you got the closed one, which is what we're looking for today. Maybe we'll get you on for episode twelve or something like that. We'll just talk about the loss aspect. Hopefully less tears though. I've cried myself, so I feel it. I can feel it.
Nolan Hansen
Perfect.
Taylor Dahlem
Well, that sounds like a roundabout way to get a neat bow tied on it. A lot of objections, a lot of barriers, but ultimately the outcome that I think helped everybody involved get to a better place, right. Solve whatever problems that are there at the same time you're winning one of.
Nolan Hansen
The bigger deals probably you've ever won, right?
Taylor Dahlem
So that being said, we always love to leave at least three tips for every Ae, every FullCycle seller listening today that maybe you experienced in this deal or any other deal that can help them move some of those deals to close one.
Nolan Hansen
Yeah. So I guess the first thing I'd say is I hope everyone understands that there's no cure-all or magic ticket to quota, right? There's no one thing that's going to jump the needle. It really comes down to consistency and discipline over time. But I felt that what helped us in this deal specifically was providing real value to them throughout the entire sale cycle, through Discovery, through the demo period, the working sessions, post, all of that as well. Just really understanding their needs, making it about them, not an interrogation, and really understanding that they have challenges and helping them uncover those challenges and solutions to those challenges. I think the other part of that is really being able to work hard for them and partner with them. So again, taking that consultative approach and becoming their business advisors I think was key. And the third thing I would say is really using your ecosystem and resources. There were so many hands that touched this deal. There has to be when we're talking about a larger enterprise deal, and whether that's our internal RFP team answering questions, building out questions, our finance team putting together multiple quotes, our CX team engaging with them before the deal is even closed as they are about to begin services, and even a trial, which, we didn't get into those details, but that was all part of it. So there were so many hands that touched this deal. And I guess would say whether you're at a small company, a large company, everyone has different resources. And so don't hesitate to take advantage and use those resources. Really use your ecosystem.
Junior Lartey
Nolan, it was really great to have you on the podcast today. If you tuned in, those listeners out there, go connect with Nolan on LinkedIn. We'll drop some links to the shows. A lot was said today. One of my favorite things, I didn't talk about this, but Nolan used the word contagious. He said the product was so contagious, it grew from fifty users to over four hundred users. Just get out there, be contagious, be contagious as hell, grow your accounts and start providing some real value. Nolan, again, great to have you.
Nolan Hansen
Thanks for having me.
Taylor Dahlem
And just like that, another episode of How Ideal is in the books. This one was quite a ride. If you enjoy the content that we're putting out in the conversations we're having, please let us know in the comments. Write us if you want, maybe a couple of stars. And please subscribe if you want to hear more from us. But thanks for tuning in. We will see you next time.