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Growing a Deal Desk Team: People, Processes, and Technology

Growing a Deal Desk Team

Katie: I’m excited to be here and thank you for unlocking a personal goal of mine, to be a deal desk influencer. It’s official as of today. So super excited to be here.

Barry: That’s one of my goals in life is to unlock other people’s milestones and influencer status. So we both win today, so it’s a good collaboration. So Katie, tell us a bit about yourself. Maybe even how you got into the sales operations deal desk world. Everyone has their own story, would love to hear yours.

Katie: Totally. I always find that it’s very rare that somebody graduates from school and says “I’m going to be in sales ops,” let alone, “I’m going to be in deal desk.” I believe everyone, myself included, has a unique story of how they ended up here. I’m happy to share mine. I graduated from school with a degree in art history, mainly focusing on contemporary Russian photography. Let’s just say that it’s a world away from SaaS and deal desk.

I started off my career working at an online art and antique marketplace. It was a super small company and we needed somebody to help out with our Salesforce instance, basically, they’re like “Katie, you’re the only one that can do text to columns in Excel. So it’s you.” That’s just the life of working at a tiny startup.

I really started my career off as a Salesforce admin, moved to Braze, and started off there a little over five years ago as a Salesforce analyst, which is really just a fancier way of saying Salesforce admin at the end of the day. A lot of the projects I had worked on, as a Salesforce analyst at Braze, were somewhat related to the deal desk.

I helped implement opportunity products, for example, so that we were able to report on ACV or revenue by each product line item that we sell. In order to do that, of course, there was a large data migration piece looking back through contracts, understanding which products do we sell and around which prices, so certainly a manual effort, but one that really put me in tune with our products and the way that we sell here at Braze.

In the fall of 2018, the company decided that we actually needed a function in-house that would not only assist salespeople in building out pricing for their contract, building out pricing for their customers, but also someone that can come in and help better automate our selling process. So, no more order forms in Word, coming up with a more seamless process for generating contracts within Salesforce, making sure all the approvals are buttoned up.

Someone that would review all of our contracts to ensure that what we have on the contract matches what we have in Salesforce, our system of record. So I stepped into that role, again, in the fall of 2018. Prior to that, we did not have a deal desk app at Braze so I really worked to define the role, the function, the scope, and build the team from the ground up. So like I said, in 2018 I was a team of one and I hired my first deal desk analyst in May of 2020. And she’s, in fact, actually now our manager of the Americas, which is wonderful to see. Since then have built out my team to be a total of 10, soon to be 11. We have a new hire starting in two weeks. There has been incredible growth in building out the team within the last two years.

Barry: Wow. Yeah. 1, 2. It took two years and then two to 11 in the past two years. That’s awesome growth and it’s awesome to hear your specific career trajectory and your history. I love that. History to the art history major.

Katie: People tell me I’m crazy, but I can point out a few parallels there. At the end of the day, to me, deal desk really is all about creative thinking, logic, problem-solving, communication, building, and defending an argument, all the same sort of skills necessary to write a good paper in college about Russian contemporary photography. It may seem like we’re on different ends of the spectrum there, but again, I’d argue that actually, it’s quite parallel to one another.

Barry: That’s awesome. Yeah, that would be a great podcast for a different time where we go through Russian photography and then on one side and you’re like, oh, this is parallel to the deal desk.

Katie: It’s been a minute, Barry, since I’ve flexed my art history skills, I graduated from college quite some time ago, but you can test my knowledge. Maybe one day.

Onboarding is the Key to Successfully Growing a Global Team

Barry: So let’s talk about that one to 11 and growing the deal desk team. What has your experience been like growing a global deal desk? 

Katie: Yes. Prior to May 2020, when I hired my first deal desk analyst, I actually was an individual contributor. I hadn’t even managed people before. I’m not really someone that does it by the book, so to speak. I spent some time Googling how to manage people and I’m like, “Oh no, this isn’t for me. I’m going to do it as I go.” Right.

And luckily, I’ve hired such incredible people that really make it easy to be a manager. But with my first hire being in May 2020, I actually hired most of my team during the pandemic. We onboarded virtually, across multiple time zones as well. I have people on my team in New York, San Francisco, Chicago, London, and Singapore. When you’re talking about Singapore, that’s a 12-hour time difference, which can be challenging, but my team and I were up for any challenge here.

And I think what’s really one of my big learnings of growing the team and something that I take so seriously going forward is onboarding. When I onboard new members of the deal desk team, we have daily one-on-ones with their manager, whether that be myself or one of my managers I have on the team, at least for 30 minutes. We have a whole rubric of topics that we cover. We do scenario role-playing as well.

I actually go back through some of the requests that have been submitted earlier in the quarter by some of our salespeople. Tweak them up a little bit and have my team members write responses back as if they were deal desk responding to a ticket or we’ll get on the phone and play it out as if we were on a call with the salespeople, just so that they, my team, feels comfortable when it comes time to actually start picking up tickets of their own.

Speaking to the sales team, they’re not thrown in the deep water without a life jacket. They’ve gone through this. They’ve seen the different types of asks and they’re confident and know how to go in and solve the problem alongside sales, which has proven to be super helpful because confidence here is really key. I like to joke that salespeople can smell fear and they certainly can, but just coming in and feeling like you know the material, you know the answer, is super helpful.

That has been one of my biggest learnings of growing the team. And it’s also, this is a little bit of more of a personal note, but for me, I’ve always found it tricky to not just take someone’s mouse and be like, “This is how you do it.” And taking that step back, because unfortunately who knows? Maybe one day in the metaverse will be able to drag someone else’s mouse with our avatars. But right now, that’s impossible. So really being able to, whether it’s by now by choice, but back earlier in the pandemic, by just nature of force, really, not having people drive on their own, and not having to step in was really big learning for me at the beginning.

Barry: That makes a lot of sense. And you’re really putting the global into the global deal desk. I love that.

Katie: Yeah. Global’s not just a buzzword for me. It’s the truth.

Barry: I love that because all you need is two countries for it to be global, but you are the real global. And then how many of the people that you hired are former art history majors or is there anyone specific or were you not looking for that?

Katie: No one on my team is an art history major. Art history majors are a small, but mighty group to begin with. I will say very few people on my team have direct deal desk experience. I have somebody on my team who is a certified lawyer in Australia. We have the full gamut of different skills. And the deal desk is very much an up-and-coming role as well.

It’s tricky to find somebody that has two to three years of direct deal desk experience working with the set of tools that we work with. It’s just really more of a soft skills assessment for me. Does this person like a challenge? Is this person able to work autonomously? Are they good problem solvers, good communicators, enjoy working cross-functionally, and supporting sales teams? Without that direct level of experience, it hasn’t been so much of an issue. And I really applaud and appreciate the diversity in the different backgrounds on my team.

Barry: Yeah, absolutely. It must be also more fun. You mentioned that the two, three years of experience, it’s hard to find those people. It reminds me of some Reddit thread I once saw looking for people with 10 years of X experience with Python and Python only existed for five years, but they wanted someone with 10 years of experience. That doesn’t exist. It’s impossible. 

Deal Desk Technology

Barry: Now we have the people, let’s move on to technology and deal desk automation. What tools or systems does your deal desk team use in order to accomplish its goals?

Katie: We recently actually just went live with DealHub, which we’re using as our deal desk CPQ tool. Prior to that, we’d been doing our pricing outside of Salesforce. There was no guided selling, less automation, and fewer product dependencies. For example, if I purchase product A, I must purchase product B and that was all done via manual addition of products to Salesforce and audits and checks by my team at the final stages.

We’ve recently moved again within the last six weeks or so over DealHub. Our sales team is thrilled with the switch. I made a hype reel, one could say, in the format of a TikTok just to psych all the salespeople up or hype them up really, and took some nice quotes from the sales team.

Some of them are saying, “I can’t believe we haven’t had this sooner,” or “I just built a quote in five minutes. This is amazing.” At the end of the day, ensuring that we are giving our sales reps time to sell and not to do admin or manual work is really important, not only to me but to our whole organization. So we’ve seen that with DealHub.

Prior to that, we had been using tools like Conga Composer, which I’m a big fan of, that allows you to generate Word documents directly from information and Salesforce. We were using essentially a homegrown deal desk CPQ that I had built, which would track all of our approvals or any changes to language inside of Salesforce and would spit out order forms in PDF format, which means as a salesperson, I can’t go in and change or add my own language.

Everything needed to be approved in the system before it is shown on an order form. Aside from DealHub, Conga, which we’re now going to move off of as we have DealHub CPQ comes with an order form or doc gen capabilities. We also use DocuSign, which we have for both internal approvals, as well as customer execution, and Braze execution of deal documents, as well as of course the big one, Salesforce. We’re a Salesforce shop here. I am a Salesforce nerd, tried and true. I’m a Ranger on Trailhead, just saying. Self-taught on Salesforce. And I have, I really have the belief that you could build anything in Salesforce that you want. So we’ve leveraged it quite a bit over here at Braze.

Barry: Okay. Awesome. Well, thank you. I’d love to see that TikTok hype reel and-

Katie: You and everybody else at DealHub, Barry.

Managing Deal Desk Process Flow

Barry: I bet, but that’s awesome. And also a nice plug. So I appreciate it. Now we’re going to move on. Before, we were talking about people, and technology, now we’re going to move to deal desk process flow. Okay? So the big three. How does your deal desk team manage request cases? I’m sure that they have a lot of requesting cases from the sales team.

Katie: Yes. As you mentioned earlier on in the podcast, I’m pretty active in the deal desk community on the Deal Desk Association group on LinkedIn, which if you are a deal desk professional and you are not in that group, I highly recommend you join it. It’s an incredible, great resource. People are always eager to jump in and help answer questions, especially if you’re newer to growing a deal desk team.

I wish I had had this resource, way back when. Anyway, the number one question people ask me, I do some meetups with people in the group. They always ask me, how do you manage requests from the sales team? Because typically deal desk teams are a lot leaner than your sales org, right? And it’s easy for things to fall through the cracks. Plus, as a deal desk leader, you want the ability to report on the number of cases, opportunity influence, whether you are meeting your SLAs or service level agreements, and so on.

We’ve actually built out this process in Salesforce. Though, you could build out something similar, whether you’re using another CRM like HubSpot or Salesforce, itself. There are a lot of different ways to do this. We actually are doing it via custom object, but you could use the case object, which is native to Salesforce as well. Essentially, salespeople will click a button on any opportunity or account, which therefore then links the case or request to the op, so we can pull in any opportunity data as well.

We have formulas that track when the case was accepted, so we can report on turnaround time. We even have something that I personally am a big fan of, called deal desk difficulty, which is a self-reported scale of one to four. So one is the easiest request and four is something that’s more difficult. It’s all self-reported. There’s no rubric because someone else’s or one person’s four could be someone else’s one, depending on tenure, experience, and so on. This has been super helpful for us, not just from a reporting standpoint, but from a bandwidth standpoint, I’m able to create reports in Salesforce and see who has what in their queue.

If one of my team members has 15 requests in their queue, another one has 20. Then I can step in and pick some up, or I could tell someone that has five, that they may need to step in and help out, regardless of what region. Additionally, as I had mentioned earlier on in the podcast, we actually use these requests to help create scenarios for onboarding new hires. I’ll go back through, look at requests that were submitted by salespeople in a given quarter and use those for our role-playing or scenarios.

Additionally, we’ll do an audit of the requests, most likely on a quarterly basis to identify knowledge gaps, process improvements, and so on. Trends, really, at the end of the day, so that we can beef up things like enablement, resources, documentation, or even if we see a certain ask to come up multiple times, how do we build that into our process to make the sales teams workflow easier and more streamlined at the end of the day. So there are just a ton of benefits to having a fully built out case or request process. I can speak to it for days. So I’ll leave it at that.

Barry: That’s super helpful. I do have one follow-up question. How long does it take to do something like that, to build the deal desk process flow? Obviously, it’s not perfect, but the first V1, how long does it take?

Katie: I would say from the Salesforce admin side, if you are an advanced, even an intermediate admin, it’s pretty simple. Like a week. It’s nothing too difficult. You’re just using, I won’t get super technical here, using screen flows, which is what is going to be the new norm for Salesforce, from a process automation standpoint, as they move from workflow and process builder onto Flow anyway, and I am also a Flow- natic, which just means you love Flow and Salesforce.

So yeah, it’s nothing too tricky. There’s tons of good documentation on Salesforce, even if you’re not a Salesforce admin, but you do have some Salesforce admin rights, or are looking for how to best direct your Salesforce admin, tons of documentation on creating screen flows is available online and it’s actually quite simple to execute on.

Barry: Okay.

Katie: Awesome. The ROI on this is huge too. The only thing I will add is then there is a change management piece here of ensuring that the sales team submits requests and doesn’t submit asks over Slack, over email, over Chatter, and really sticking to your ground that if a request comes in via Slack, or to you directly, I’ll just say, submit a request.

At the end of the day, it’s actually, if you’re in sales or any other team that the deal desk supports, it’s in your best interest to do so because the request goes out to the entire global team, right? So you’re better off sending a request to 10 or 11 people than just one person. Especially when you have a global team that covers 24 hours a day, it’s anything that is left in the queue from the EMEA teams in the morning, America’s teams can pick up. Something that’s leftover from the west, my Singapore or APAC team can pick up.

You’re better off sending out something that gets sent to multiple people than just one. You really got to sell it to your users as well and stick to your ground to ensure that you’re not continuing to answer via email or via Slack. Instilling those good behaviors in the teams you work with is key to ensuring that this is a success.

Barry: That makes a lot of sense. I was thinking back, I used to work at Waze and because it’s like a B2C product, everyone just talks to you as if they’re your friend and that you can actually make changes. So you’re like “Waze took me to the wrong place today. Fix this, please.” I’m like, “I’m in marketing. Here’s the link. Maybe you downloaded it because of me, but you definitely didn’t make the wrong turn because of me, I don’t even know who to talk to. Here’s the link.”

Deal Desk Pain Points

Barry: Let’s talk about pain points in the deal process. We talked about people, we talked about tech, and we talked about processes. Now let’s get to the nitty-gritty. Some of the points on the deal desk could be 11 persons’ pain points or one person’s pain points. And what have you done to alleviate some of these pain points?

Katie: I think, and I’ll speak more generally towards all deal desks perhaps here, but accuracy is certainly a pain point. We’ve used this expression here at Braze, but I think it is applicable to all deal desks. In fact, my team jokes sometimes should we get this as a tattoo, but maybe we should, but it’s ‘slow is smooth, and smooth is fast’.

What I mean by that is if you, especially at peak times, like the end of the quarter, you have all these salespeople breathing down your neck, essentially, saying “The customer’s waiting to sign this right now. I need you to do your review as quickly as possible.” So you have pressure. You’re trying to move fast, which leads to mistakes, right? Especially when there is more manual work required on the salesperson’s part, whether that be entering in products manually or generating contracts or order forms manually, filling information on an opportunity in Salesforce manually, right?

Wherever you do not have automation and you have manual input there’s room for error, right? So we’ve moved to CPQ most recently to DealHub, at that, which helps us better automate our systems and tools to ensure more accuracy. There will be a day further down the road where, everything is super buttoned-up, the system doesn’t allow for anything to be entered incorrectly, and we would need to spend even less time on our reviews or even make said reviews go away altogether. There’s also, it’s difficult to measure accuracy as well, right? So how do I identify where mistakes were made, what the mistake was, and then either, how do I better train my team to avoid said mistakes in the future, or how do I create better resources and enablement to prevent salespeople from making those mistakes?

Accuracy is certainly a large one. I don’t have an answer for this one. Its point two would be working on deal desk is certainly a very cross-functional role, right? So you’re at least, Braze, our largest customer is the sales team who we support in order to best structure their deals, help with more non-standard order forms or even signature processes, what have you.

But that’s not to say that we don’t work with nearly every other team in the organization, right? Most closely after sales being legal and finance. At the end of the day, a lot of these different branches, if you will, legal, finance or accounting and sales may all want different things. So coming up with a solution that works for all three parties really, fits within your company’s acceptable policies and guidelines and communicating that across teams is certainly a challenge. But one that I would argue makes the job more fun.

Barry: Absolutely. Cross-team collaboration, you hear it over and over again. So it’s definitely not just Braze. It’s every company. 

Katie: No, at the end of the day, it really does make a lot of sense, right? Because when you take your time and do something accurately, that saves time in the long run, versus if you rush, you make a mistake, you have to do an amendment, then you’re actually spending more time not selling than if you spent the extra 15 minutes on your review to ensure that everything was accurate and there were no errors.

Everything on the contract adds up correctly, and the data and the opportunity match what’s on the order form. It’s all buttoned up, way better off to take that extra time, slow is smooth, and smooth is fast. That’s why you should title this episode, by the way. ‘Slow is smooth and smooth is fast’ with Katie. No, but yeah, it really does save you time in the long run. So, ensuring that your team isn’t rushing and that they’re able to kind of push off or brush away any pressure from other teams is really important.

Barry: I love that. As a product marketer, I remember doing this one exercise more than a year ago, but I was trying to say that go fast with your sales proposals, you can create your order forms fast with DealHub CPQ, et cetera, but then there’s like, anyone can do anything fast. It just might be terrible. So it’s that differentiation of, yes, you can go fast, but then it might be really bad. So slow is smooth, and smooth is fast.

Katie: Right. I even think as it relates to like metrics and the reporting on the cases that we touched on earlier, it’s even having, we call them OKRs or goals or objectives for your team. I’m always a little wary to put in meeting SLAs because I don’t want the team to rush to meet their service level agreement. So for example, that request will be done in two days. I don’t want someone to rush through to meet that goal. But if in fact, it actually will take them longer. So it’s important, I think accuracy over speed any day.

Barry: Absolutely. It’s a little different, but I once watched a webinar from monday.com on customer success and they were talking about, if you have this SLA, they didn’t call SLA, they call it KPI. But if you have this KPI, then you might end up with the wrong thing because the objectives are different. They’re just trying to go faster and you don’t want that if there are going to be mistakes.

Onboarding Process for New Deal Desk Hires

Barry: So what is your onboarding process for new deal desk hires entail? What are the processes? We touched on onboarding before, so maybe there’s not too much more to add, so if you don’t have anything else to add, then don’t worry about it, but would love to hear some more processes if there is anything specific you’d like to add.

Katie: I can’t emphasize this enough, but onboarding is so important to ensuring the success of your new deal desk hires. You want to make sure that they are confident and comfortable when it comes time for them to fully go out on their own and you got to walk, you got to crawl before you can walk, walk before you can jog, and jog before you can sprint. Typically, we are a SaaS business, we’re both new business deals as well as renewals and upsell.

We’ll actually start off on the simpler side of the business and then move on once the new hire shows mastery and understanding of new business, we’ll move on to some more complex renewal and upsell deals. At the end of the day, you just want to make sure that you’re getting those quick wins and those confidence boosters first, before you move on to more challenging material, taking somebody who’s on week one and putting them on the most complex deal that the team is working on this quarter is probably not the best idea, right?

You want to start small, not only to ensure that they have that confidence but really to build the foundation, the building blocks before you can start to tackle more complex deals. If you’re using Salesforce, I would also recommend giving your team or new hires, Sandbox access. So they can go around and play by putting themselves in the salesperson’s shoes. Maybe move an opportunity through the entire sales process and see which fields they need to fill out before moving to a certain stage and being able to empathize with the teams that you’re helping too, is super important.

I think I covered a lot of the onboarding stuff earlier on, just by nature of the conversation, but I’m a huge believer in, and I hate this phrase, but I don’t know, if you think of another way or another way to say this, please let me know, but teach a man to fish, right?

Go through the steps as if they are dealing directly with the salespeople so that they have that knowledge, they have that confidence, to go out into the real world. Now I’ll like to send them off to college, to go work with the sales team. It’s definitely an investment, but one that I would argue has made my team so successful and at the end of the day, respected across the whole sales organization too, because everyone knows what they’re talking about, by the time that they go into the field.

Barry: Right, absolutely. Then how much time is that, usually?

Katie: I don’t really like to put a time. People learn differently. I wasn’t an education minor, but I was one class away from one. So you could say I was close, but I am someone that really believes in different learning styles and learning paces. I’ve onboarded at this point, upwards of eight people, maybe a little less on my own. It’s a blur right now, but everybody’s onboarding goes a little bit differently. You could be having a conversation naturally, just like how we’re having. A question comes up about another topic that would, we would cover later on down the list, right. I’m not going to say, not now, that’s for week seven. If it’s coming up naturally and if the new hire is asking that question, let’s address it then and there.

Typically, I’ll say if you did ask me to put a timeframe on it, I would say 90 days. Though, some people move quicker than that. Others take a little more time. At the end of the day, I want that person to tell me I’m ready and I don’t want to push people if they don’t feel like they’re up for it quite yet. If we need to do a few more scenarios. But for the most part, my team has gotten up to speed within, I would say, even less than 90 days, most people.

Barry: Absolutely. If anyone’s listening that’s an entrepreneur, some good tech to do role-playing in the deal desk kind of thing. I think that could be a cool gamification kind of thing going on over there.

Katie: I actually did gamify it. For one of my new hires, I created different levels and he always puts it in a gaming chair. I’m not a video gamer, but I’m a phone gamer, but that’s for another time. But I had all the different levels as different tracks in Mario Kart, like the most difficult level was Rainbow Road.

Just to make it a little bit more fun, I would say, I love a good gamification moment. Hence, why I am a Ranger and Trailhead, because I just needed to get to the next badge if you know what I mean, all my other Rangers or Trailheaders out there, but yeah. Make it fun too because I also believe that people do the best work or do their best work when they enjoy what they’re doing.

You could cater it to your different team member’s interests, but is it also fun for you as the hiring manager to take a little step back into memory lane and think about what courses of Mario Kart were the most difficult for me?

Barry: What do you look for in your deal desk hires?

Katie: I think I also touched on this a little bit earlier on the podcast, but what I said earlier was, that it’s hard to find people that have the direct deal desk skill because it is such a new or niche industry. So really what I look for is somebody who is excited by a new challenge or a new problem to solve, that the most difficult of requests or asks from the sales team are actually the ones that make you jump out of bed in the morning and that you’re ready to go tackle versus not wanting to pick it up because you’re like, “Oh no, this is going to be too much.”

Someone that loves problem-solving, loves a challenge, and loves doing something new every day. Because I can tell you and I’m sure most deal desk professionals would agree. No day is the same. You think you’ve seen every creative solution from salespeople. But let me tell you, you haven’t. They will think of something new. Somebody that enjoys that challenge, somebody that can work autonomously and with pretty little guidance, especially when you’re talking about time zones being quite far away from our HQ, which is in New York, and somebody who is a good communicator is huge, both written and verbal communication.

Because I look at deal desk almost like the command center really. You’re helping the salespeople to understand how we got to a certain number for pricing, how the pricing works, and how to defend that pricing to a buyer or to a procurement team. Being a good communicator is super important.

And finally, this one’s a little bit more of a softer skill and I don’t want to give away my interview question that I always ask, but working really closely with the sales team is huge. Somebody that will enjoy working with sales and that sales will enjoy working with. Because I believe that having the ability to build or forge trusting relationships and genuine relationships with your end-users or customers, which for the most part, in our case, is the sales team, is so important for a few reasons.

One, it makes it easier to shut it down. When the sales team is being creative, it helps garner, respect, and trust. And lastly, it makes your job more fun, if you enjoy the people that you’re working with. So that, to me, is somebody that I can picture working really well with our sales team and that I can picture working really well with our deal desk team, our larger revenue operations, and finance teams is really key to me as well.

Barry: Awesome. Well, Katie, I feel like we’ve developed a genuine relationship during this podcast. Not saying that I’m applying for a deal desk position, but I really enjoyed this conversation. You obviously have lived up to the word I heard beforehand from my team and from some people externally so thank you for that. Looking forward to seeing the Braze team continue to grow.

I want to thank our listeners for listening. Katie, if they have any questions, where’s the best place they can reach you?

Katie: They can send me a message on LinkedIn and we can connect from there.