#040 From ABC to Always Curious with Shai Haddad

A Deep Dive into Revenue, Operations, and Curiosity

Guest & Host

Shai Haddad & Thomas Miltschuh

Welcome to Speak Revenue, the podcast where we emphasize that revenue is not just a goal; it's a result. In this show, we shift our focus from the output to the inputs. We engage in conversations with sales leaders and entrepreneurs about their remarkable journeys. Our mission? To uncover the true root causes of success. Join Thomas Miltschuh in an enlightening conversation with Shai Haddad on the latest episode of Speak Revenue. Dive into the world of revenue and operations, where Shai shares his 30 years of sales experience, emphasizing the power of curiosity, data analysis, and customer-centric approaches. Discover the challenges and triumphs of steering Update Capital, an investment platform, towards success. Uncover valuable lessons on minimizing noise, fostering collaboration, and staying relentlessly curious.

November 14th, 2023


Thomas Miltschuh: Welcome to our new episode of Speak Revenue. Remember, revenue is not a goal. It's a result! But a result of what? In this show, we turn our eyes from the output towards the inputs. We speak to sales leaders and entrepreneurs about their journeys. Join us on our quest to uncover and learn the root causes of success. Let's unpack what works for them. And what didn't! Today with our guest, Shai Haddad. Hello, Shai. Great to meet you. Welcome to the show.

Shai Haddad: Thank you, Thomas. Thank you. Thanks for having me.

Thomas Miltschuh: Could you please let us know to get started? Who are you? What do you do? Why are you so successful?

Shai Haddad: That's a packed question. What is success? I'm based outta Montreal. I've been in sales, roughly 30 years, but in, in Tech and in B2B Tech for about 15. And I think what has helped me through the years is just starting out in the early nineties, pre-technology, pre-internet just learning the craft of conversation and asking good questions. And staying curious, you know, is a big driver for me. There's an old sales mantra called "Always Be Closing" - ABC. And I think today it's always curious. I always share that with my teams. So that has been a big piece of it. And I really I'm a bit of a data geek nerd, so I like to get into the weeds. And then the last five years really getting into the analysis of data and what leads up to the outcome of revenue to identify things. So, that's where I'm at.

Thomas Miltschuh: Great. Sounds like you really have a lot of experience to share. Looking forward to that. What's your current role? 

Shai Haddad: Current role is a mouthful, but I oversee revenue and operations. So as Chief Revenue and Operations Officer for Update Capital which is an investment platform. It's a portal for private equity and real estate for investors.

Thomas Miltschuh: Great. What do you, please let us know what are your goals for this year and the next year?

Shai Haddad: Oh. So this is really a startup in every sense of the word. It was acquired by a large gen two, which is a really large fund administrator. The goal I think, for the remainder of the year for me is to stabilize and strengthen current. delivery of value to customers and really maximize the value that our users are getting from the platform. For next year it's one of, one of the greatest challenges I think. In my experience it has been just moving up market. How do we start increasing our ACV and thinking about new opportunities? So it will require a lot of segmentation

Thomas Miltschuh: Okay.

Shai Haddad: Next year it's really moving up market and exploring new segments within private equity and real estate that we can cater to and deliver value. It's really a massive TAM and we gotta carve it out, not just quote unquote spray and pray, or rather we be very mindful and find the right segment and start moving up. Upmarket it's starting to come together really nice and I'm surrounded by incredible people. So it makes such a big difference, analysts and people with years of experience and leadership and in the private equity space and incredible developers. So it helps alleviate a lot of the day-to-day and starting to think about where we're headed.

Thomas Miltschuh: Nice. Sounds like an exciting journey. So what's your approach to stabilize value delivery? Any framework you can suggest or mention.

Shai Haddad: Yeah, I, it's interesting, this is the first time in a while that I'm learning to really get, understand the nuts and bolts of the business and clients getting really granular. I think especially in SaaS and in the past few years personally I didn't do it and I think I could have benefited from doing so. It's just getting a little bit more granular, a little bit more micro into understanding each client's needs. At the beginning, before you start really scaling at mass. So stabilizing, I'd say it's, analysis. I see it as going to the doctor first. There has to be a diagnosis, right? Before a recommendation. And in order to do a diagnosis, you gotta run a bunch of tests. You gotta ask a ton of questions and rule out any potential threats or issues or concerns and identify real threats, issues and concerns. So diagnosis, going back to curiosity is definitely a part of the playbook in this case. And then identifying those things that are high impact. We often do. And focus on the high Impact activities. What I mean by high impact activities is that, one single thing that delivers most value, it's the 80 20 rule, like focus on the 20% that will deliver the most value. The sooner you do that, the better. Get that, build that confidence for your customer, especially when you're speaking about large scale customers. Enterprise, 2/ 3/ 400000 dollars ACV, you have to dedicate, sometimes mobilize your entire team to do that. That's of course resource constraints and you have to be mindful, but in a nutshell, get in there, identify what creates the most value, deliver it immediately, and then build a plan for the rest so that, that creates trust, right? So you also do things. And grow. So, the first piece and the last piece is really being radically transparent with your customer. There's so many times you want to please and you say yes, to things that are creating a lot of work for your colleagues and the rest of the company. It's not always, it's not always great and then things could fall behind. You wanna be able to be very transparent and walk your client through. The steps, and what it takes to get there so that they're part of the journey. It's amazing how many clients, you know, we're still, it's technology, but it's still humans. And there's an empathy when you start creating that collaboration, there's an empathy that gets built and there's a desire to actually work together better. So it makes future conversations a lot better. So There's no beating around the bush. Eventually, what happens is gonna float back. You might as well lay it out early on.

Thomas Miltschuh: Yeah. Yeah. That's right. So talking about those steps together with the clients, how does your sales process look like currently it's a early stage

Shai Haddad: Yeah.

Thomas Miltschuh: very dynamic environment for your team, probably. How does it look currently from lead generation or closing to upsell? And maybe as a next question, where would you like to be in a year? What would you like to improve there?

Shai Haddad: That's a good question, Thomas. Early on in, and I've seen this in the past where, when a product is launched and you're really trying to get product market fit you'd be more successful. This is my personal opinion again. I am thinking about founder-led sales, when the founder is involved in the early stages of the sales cycle and the sales process. That passion, that belief, right? The product and what it brings to the market is super important. And that's been the case with our portal. And a lot of it was found to lead. And once we really identified a product market fit now it's time to start thinking about other markets or other market segments that we can attend to. And this is, I'd be lying if I told you. Now I know exactly how the sales process is going, because we're learning.

Thomas Miltschuh: Sure.

Shai Haddad: But there's definitely identifying those 10 x superstar kind of account executives out there that have experience in the market. This is a very specific, private equity space. And I don't actually have that background actually. I'm new to space, so Understanding the space and surrounding myself with people who do I think is crucial. So hiring for that, is a big piece. And then the ability to... There's a lot of farming involved, post hunting. So yes, getting a strong hunter is really important, but really farming and developing that relationship and that stickiness. You know, these are customers that will stay with you for 3, 5, 10, 20 years. There are existing customers of the fund that have been there for quite a while. So how do you... How do you make that parallel between the services that you're offering and the technology that can deliver value to keep them, is part of the sales process. So even at the first conversation with a potential client, you have to start , it's such a tight-knit community that you have to start with these kinds of referrals. Who knows who. So it's not very different from going out there and starting a performance marketing lead gen campaign. I think you have to start with existing clients, their counterparts, start having these conversations and build a solid starting point and a pool of clients that are established.

Thomas Miltschuh: Sounds it's a phase of establishing processes 

Shai Haddad: It is. Yeah. And it's very different from past experiences that I've had where the SaaS playbook model was a lot clearer and less nuanced. And here, there's an overlap of services, there's an overlap of technology, but also it's a space that is I guess later to the game when it comes to leveraging technology.

Thomas Miltschuh: Is it something new maybe? Yeah. New business model as well. Do you have some tips for the audience for getting started in new roles and switching doing the transition in the best way? 

Shai Haddad: I do. I think we take on a lot when we come into a new role. We wanna show value in so many things. I believe today after learning the hard way, I believe today that it's better to go deep on one, really one aspect of the role. Go really deep. Understand it from start to bottom whether it's customer success or marketing or the sales model or operations or billing, right? Find it, speak to the right people, ask the right questions. Get everybody together also to have these conversations. Don't keep it in silos, right? So go deep, take things from start to finish. Tick them off. Otherwise you'll be working on 5, 6, 7, 8 things and they'll stay at 20, 30% and you'll never get to the end of it. Never, not never, but it'll be longer to get to the end of it rather than say,: Hey Thomas, let's understand the billing process. Okay, well, let's get our accounts receivable person, or let's get the CFO into the conversation. Let's understand the whole process. Let's map it out. Let's identify. Some threats or some issues in that process and how we can improve them, get in there, build up the processes, make sure they're working, test them out, you know, stress test them, and then move on to the next thing once that is running. I would say that would be really my advice as you're starting out. And it will also help. You are more familiar with different parts of the business. Nobody expects you to know everything the first day. Maybe some people do, but most people don't expect you to know everything the first day. And we put a lot of pressure on ourselves in leadership to show. But showing curiosity, I think and getting to ask the right questions is as important and in many cases, more important.

Thomas Miltschuh: So how do you prioritize, probably also related to the 80 20 rule. So what, how do you find out the most important things to get started? 

Shai Haddad: Man, that's... I can't tell you that I have a, playbook

Thomas Miltschuh: It probably really depends on the specific role and company.

Shai Haddad: Indeed. But I think every time you have these conversations, you start to. Appreciate and identify these things that are... the priorities start to change. You know? What do I usually like to do? I really put a list together, literally like a laundry list, and I put it into P1, P2, P3, priority one, priority two, priority three, and then you know, those priorities start changing. So that's in the diagnosis phase. Once I'm done with that, then I can move into actioning based on the priorities, so not to be too theoretical. Essentially there are things when you really map out and ask the right questions and you document everything and you start putting time to it. So it's not just the action, it's how long it takes. You'll find that some things are taking 12 hours where they can take maybe three hours. Is there any way to make this better? Is there anyone in the company that would know how to maybe it's a process, maybe there's something we can automate, maybe, data extraction can be done through technology rather than with a person. Maybe the sales cycle is taken too long at the discovery phase, and we don't need it to be too long. So until you map it out, you don't know what's gonna be prioritized. But I believe that after, once you identify the time and the conversion from one point to another, then you can start thinking: Okay, this will have the highest impact in terms of not revenue as the end goal, but actually leading up to accelerating the path to revenue or to make it more efficient or creating value for the customer. For me, the value that the customer gets from the product is a benchmark for the priority. Like how soon and how impactful can we show value to the customer? Is this how I like to prioritize things? Then revenue will be the end result of that, right? Revenue will come from that and keep growing.

Thomas Miltschuh: Yeah.. The goal must be the orientation or give the orientation, right? Let's talk about tech stack a bit. But what tools are you using? Do you see general differences? On different kinds of tools used in enterprise sales compared to, let's say, more, more transactional SaaS sales.

Shai Haddad: Yeah. Yeah. I do see a couple of differences, I think, philosophically I believe that the less tools, the better.

Thomas Miltschuh: Yeah.

Shai Haddad: I've been in organizations where, sometimes there's more tools than employees. And then, this team, like this tool, this team is like that tool currently I'm leveraging with the team, we're using Slack, but we're also using Teams for other things. Might be some overlap, something to think about. The CRM we have Of course Salesforce for part of it, for the services. And then we have another CRM called Close for managing some of the customer engagement stuff. Lots of tools on the product side and on the engineering side. So it's pretty large, it's a pretty heavy tech stack. I think that as you grow and you come in and you start thinking about operational efficiencies, you're always going to find some overlaps. I don't think you need to compromise and remove tools just to remove them, but staying lean is finding these overlaps. Again, going back to diagnose, find some of the overlaps and you might be, it's not just the cost of the tool, it's also training on different tools and switching between them Things can fall between the cracks, like just the more it's concentrated in one area and easier to access by anyone. So think about tools that are collaborative, that are lean, and as you grow that are highly specialized. The more you grow, the more specialized the tool. In the beginning start general. You don't have to have so many tools when you start out, you can have a one kind of solution that covers a lot of the tasks.

Thomas Miltschuh: Seems like in general one of your top priorities is to reduce waste, right? Or…

Shai Haddad: Yeah. 

Thomas Miltschuh: …minimize waste as much as possible?

Shai Haddad: Yeah, minimize waste or as my former colleagues would tell you, I like to kill the noise. There's a lot of noise often and not because people wanna create noise. It's just, people wanna do good. They wanna help, they wanna provide inputs, they wanna share their experience. They really want things to get better. And sometimes we get lost because there's so much to do. When you're starting, there is so much to do. So how do you kill that noise and say, this can wait until Q3 next year. This has to be done tomorrow. This can wait until... and I think that's where you can help your team and shield them from a lot of this overwhelming, as an individual contributor, if you're getting all these things coming your way, it's not enough hours in the day, how do we help? Our teams really stay still on track. And also it's a great feeling to say: Oh, I got this done today or this week. There's a wonderful book that I really love. "The 4 Disciplines of Execution" and they talk about the wildly important goal. I dunno if you had a chance to see that concept. So really having those on a daily, weekly, monthly basis, even yearly has been super, super valuable for me. I had a great mentor a few years ago that introduced me to that concept, so really defining what's your wildly important goal for this. If all hell breaks loose, what is the only thing that needs to really be done that really helps reduce waste and noise?

Thomas Miltschuh: Great. Who's the author?

Shai Haddad: That's a good question. 

Thomas Miltschuh: We will have to look into it…

Shai Haddad: The name of the author. 

Thomas Miltschuh: No worries. We'll find out. Yeah. Cool.

Shai Haddad: The concept is great.

Thomas Miltschuh: Great. As you've mentioned, things you've learned the hard way, what do you like to share with us something that just does not work?

Shai Haddad: Oh wow. Let's think about that for a second. Well, I Think in my previous role, I kept a lot of things high level in terms of the customers, like understanding the customers. And only towards the last few months I started going in and meeting and speaking with customers. I should have done that better, in my opinion, early on to get into the weeds and just. Really not be afraid to dig in and go and speak with customers directly. It's the wealth of information that you can get from a customer. And, that's something I learned the hard way and it led me to really get in these conversations and actually ask our customers for them to demo the product to me. So a reverse demo and watch them use our product. Watch them use our technology. I call it a reverse demo. it probably exists somewhere, but for me, a reverse demo allows you to know, somebody might be using the product in a way that you haven't even thought about. And that's great input for your product team. That's great input for your Go-to-market. That's great, something you can leverage for other customers. You'll be amazed at what you're gonna find out. So that was something that I think I didn't do enough in the past and I definitely wanna already be doing more now. I hope that answers the question.

Thomas Miltschuh: Yes, sure. But I'm wondering, yeah, how and when you realized you needed to change something, what was the trigger?

Shai Haddad: I started getting more involved with customer success. Later in my career. I was really responsible just for sales for a long time, and then slowly into go-to-market motions. And then about three years ago, I started getting into customer success. And I made the mistake of looking at it very similar to other, other motions. And it's not, it's really your customer's success. You need to understand what makes your customer successful and how are you gonna do that if you're not talking to customers. So it's harder to do in, let's say, product led organizations or really. High velocity sales where you have a, inbound motion and low ACV 500, 600 MRR, or, $2,000 in ARR, whatever that may be. It's harder to do, right? You can't speak to a thousand clients, but as you move up market and you start dealing with large clients, you can benefit from doing that at all levels. Don't leave it up just to your CSM work, work with them, work with the entire customer success team. Go on a roadshow and see your customers. I had so much value from doing that and with our CSM and with our head of product marketing actually, and our head of engineering we went on tour. Literally. We visited about 18 clients in a short period of a couple of weeks. And every day we saw one or two clients, really, we got to the airport, rented a car, and just drove an incredible experience. So what led to that was really getting to customer success. And I, after 2, 3, 4 months, I said, I really don't get it. I'm missing something here. I see the reports,

Thomas Miltschuh: Okay.

Shai Haddad: I ask the CSMs, the questions I get on client calls. But once you start getting really deep and doing the reverse demo and asking: Hey, show me how you log in? How are you even logging into the platform? What's your home screen setup? Incredible wealth of information that sits with our clients and we can really benefit from doing that. So I learned that at that point.

Thomas Miltschuh: Do you apply the "Jobs To Be Done" framework as well? If you're familiar with that? 

Shai Haddad: Absolutely. Yeah. So that's one of the things that I was trying to get out of in the reverse demo. It's, don't tell me the features you want, show me what you're trying to accomplish. We'll talk about what the feature is called later. It doesn't matter. It's really what are you trying to accomplish and how do we get you from A to B in the easiest, most efficient time, right? Efficient way. It's definitely around that framework rather than features and functionalities.

Thomas Miltschuh: Maybe a last question to finalize the episode. Is there any other lesson learned you would like to share with the audience? Something that comes to mind.

Shai Haddad: Yeah I've said it before, but really stay, staying curious and asking people around you, I think is one thing, but also get people involved, ask for help. There's no shame in that game. It's very beneficial for everyone if I'm trying to tackle a solution. There are likely people in the organization that can get together with you, help you think about it from different angles. The synergies when people come together are exponential. There's no way that I could solve something from start to finish by myself efficiently as I could with other team members. And, to be honest I didn't always do that. I always try to tackle things. It doesn't work. It doesn't work. There's a really wonderful aspect of collaboration and subject matter experts that you can bring in and say, Hey, Thomas, what do you think about this? And you'll get really good perspectives.

Thomas Miltschuh: Yeah, I think also external people can bring a big value there. Just outsiders looking in, that don't know every detail.

Shai Haddad: Yeah, that's true. That's a really good point. Yeah, you can really get a fresh perspective. You stay curious, you collaborate, bring people and silos are created organically. It's not something that people are, oh, I wanna work in a silo. I don't want to collaborate, it happens. Encourage yourself to really break out of it. Do I have everyone on this call that really helps? Am I speaking to the right people, am I asking the questions? You know, keep challenging yourself.

Thomas Miltschuh: Yeah, definitely. Fantastic. All right everyone, it brings us to the end of the episode. I want to thank you Shai Haddad for joining us today, sharing such valuable insights. Huge shout out to all our listeners. Your support means the world to us. Remember to check out our website: speakrevenue.com for a full transcript and additional resources, and if you enjoyed the show, please leave us a review on Apple Podcasts or wherever we go for your listening needs really helps get the word out. Also, follow us on LinkedIn and Instagram or on YouTube. We'll be back soon with another great guest. Until then, stay curious. Keep listening.

Copyrighted © 2022-23 Jaxx Technologies, Inc.

Copyrighted © 2022-23 Jaxx Technologies, Inc.