About the speaker

Natalie Peled David was a GTM leader for PX, a Series A start-up in the MarTech space, and she now advises early-stage companies on their go-to-market approaches. While leading Sales and Customer Success in her last position, she learned how customer success is at the intersection of everything that goes on in an organization and the impact CS has on revenue.

Effective Customer Success Strategy and GTM Motion

Barry: Can you tell our listeners about your background in Sales and Customer Success? And, what is a customer success strategy and how does it relate to GTM motion?

Natalie: I was hired by PX to basically build out the initial Sales team, sales strategy, and prepare the company for scale. And I did that successfully for the first three and a half years that I was at the company, with some ups and downs and no shortage of mistakes along the way. But we were able to hit our goals, bring in great new clients for the company, demonstrate a lot of added value to those clients’ businesses and grow on the front end.

What we noticed was that we also had a lot of great long-standing clients and a lot of success in terms of managing those relationships over time, but we needed to unify our go-to-market strategy. We needed to have one synced approach to how we were going to land clients and expand those relationships over time. And so, after about three and a half years, I was tapped to take on the challenge, take on the opportunity to manage Client Success as well as Sales, and unify that under one whole kind of go-to-market revenue approach.

Barry: Let’s go into those details. Would that include more upselling? Is that selling new products that they didn’t sign for originally? 

Natalie: We had a combination of a fixed fee and a usage-based component to the way that clients could use our services and solutions. And what we wanted to see was how we could drive clients to greater levels of usage, but also more strategic commitments to how they were going to embed the platform into their ongoing business operations. And so, it was really about selling more strategic, more sticky elements of our products and services to the existing clients, and getting them to adopt our solutions more broadly.

Barry: Cool. So, really increasing the revenue across multiple products, if you will. Let’s talk more about that. What surprised you when you first started in the customer success position? 

Natalie: I can tell you that I had always had a lot of admiration for Customer Success teams in general. At every point having been in sales and having had to rely on a very strong customer success team or account management team to help grow and cultivate those relationships and deliver value realization and deliver impact to the clients, I had always had a ton of admiration and respect for how challenging that role was. And I think that in the transition to managing Client Success, that just deepened.

A conversation that I had with my CEO pretty soon after that transition, I said to him, “Wow. That is the hardest job in the organization.” And it’s not that Sales wasn’t hard. It was just with Client Success, they were essentially at the intersection of every single thing that was going on in the organization, for better or for worse. And so they had the incredible responsibility of handling, fielding, troubleshooting, managing any situation that came their way, whether it was a client who was excited about the way that they were experiencing our product and wanted new features and functionalities built on or whether it was a client that had a concern, CS needed to be at the front lines of all of that and maintain their cool and maintain their professionalism. And I just had, and continue to have, really deep respect for how multifaceted they needed to be.

Finding Your Ideal Customer Segment 

Barry: That gives us the surprise from the role of Customer Success Managers. Now, any surprises about customer expectations after they purchased the product that you had to deal with?

Natalie: I think what we learned was that we had initially had a broader approach to which kinds of clients we thought we could serve well long-term. And over time, we came to really segment our successes more specifically and understand which client profiles we were best equipped to successfully serve now versus later, and having to make some of those tough calls around what that meant.

So if we weren’t able to do a good job with a certain segment of clients now, what’s the lift? What’s the work that we’re going to need to put into it as an organization, whether it’s headcount, whether it’s new elements of platform features and services, whether it was a support layer that needed to look different, and were we prepared as an organization to make those investments? And if not now, then when?

There were some useful insights there around where can we really be most effective and where can we be the best fit for our clients today versus what are some of the clients that we might need to say no to in the short-term and how do we bring those insights all the way to the top of the sales funnel so that we don’t have that kind of breakdown communication once they’re already signed a contract or something like that.

Barry: That’s interesting. If you weren’t in Customer Success and with Sales, do you think it would’ve been harder to communicate that, that holistic approach, to be able to bring that back to the sales team or do you think it would’ve been the same? Were there any different biases you had because you were on the Sales and the Customer Success teams? Good biases or bad biases?

Natalie: I think that’s a great question. I think you’re always shaped by your perspective and your understanding of the situation is often going to be shaped by your perspective. I can say one of the things that I’ve cultivated over the years, for myself and certainly for my team, is trying to understand the broader context in which certain decisions are made or the broader context in which organizational choices are considered.

And I do think that while, as head of Sales, I did have a very company holistic approach and what’s going to be best for the company and its growth. Yeah, I think the perspective that shifted once I was a little bit deeper into the trenches with the Client Success team was an understanding of when certain clients are not successful it’s not because X, Y, or Z didn’t do their job well, or X, Y, or Z dropped the ball, right? There are a lot of opinions that you can have when you’re on the other side of a certain situation, and I think that unification of the teams and the aligning of the perspectives of the teams definitely helped me see that differently. When I realized it wasn’t a person problem, it was more of a kind of organizational problem that we needed to solve through making some tough choices.

And yes, I think by the time I had made that transition, I had earned enough trust from the Sales team that when we had to have these conversations around, “Okay, certain client profiles may or may not be a great fit for us, and therefore here’s how we’re going to adjust our pipelines. And therefore, here’s how we’re going to adjust our conversations and even our pricing models,” there was more credibility to go along with that.

You may also be interested in: How CS Can Drive Revenue From Existing Customers

How to Scale Customer Success

Barry: Absolutely. Let’s say you don’t have that luxury of credibility or that trust, how could someone in Customer Success make it easy for sales to understand, or do they really just have to go straight to management who has more of that holistic view to be able to create that change management?

Natalie: I think creating visibility and transparency can go a really long way. I think one of the things that I noticed, our Client Success team at the time, they were so busy and they knew a lot of the answers. They knew a lot of what needed to change, but they were so busy just managing all the things that were happening on their plate that taking a moment to stop and consider how somebody else, who wasn’t in the trenches with them, might perceive a decision to, let’s say, stop serving a specific client segment. They didn’t necessarily think, how can we present that information transparently? How can we make this a bit of a business case? How can we show the raw data that’s leading us to the conclusion that will ultimately be able to serve more clients more effectively if we isolate this specific subset?

And so ultimately it came down to just documenting a little bit better, even in like a rough Excel sheet. But documenting, here are the clients, here’s what’s working well, here’s what’s not working well, here’s what we’ve tried, here’s our proposal. And then, being able to share that with the Sales team where each of the people involved has a vested interest in this client, that client, that deal that I brought on. But then being able to see how it played out and being able to see how much time and attention and dedication each of those clients really had been given. It can allay some of the concerns around, again, is this a drop the ball situation or is this an organizational decision that we need to make so that we all succeed?

Barry: That makes a lot of sense. Recently, I started taking that one step back, and it just has propelled my work further because now I’m accomplishing more for the company by proposing business cases and use cases and challenges I had and how to overcome.

Natalie: I was just going to say I recently heard somebody articulate this pretty well. It’s a lady named Alli Rizacos, and she’s actually an imposter syndrome coach and leads some great workshops. But she recently talked about kind of one of the ways in which this plays out is that you assume that the things that you know, everybody else must know. That’s one of the ways that you sometimes can diminish yourself or develop that sense that, okay, maybe I don’t have the most brilliant insights and maybe it’s not worth sharing. It’s out of this assumption that, well, if I figured this out, probably all the other smart people in the company or probably all the other smart people in my department have already figured this out, so it may not be worth saying or it may not be worth presenting.

But I think that’s, again, where people in the organization need to recognize that everyone’s coming from their own perspective. And sometimes it really can help to build consensus or new awareness when you take the time to walk other people through, not only your conclusions, but the data and the observations that led you to those conclusions and then bring them on board.

Becoming a Process-Oriented Salesperson

Barry: Let’s build on our conversation to more processes. We were talking before that you are a process-oriented salesperson. It’s not something you see in every salesperson. I would love to hear how you became a process-oriented salesperson and what that even means for our listeners.

Natalie: I think we’re seeing the rise of more and more process-oriented salespeople, hand-in-hand with the rise of the RevOps function as a whole. And recognizing that when organizations need to grow, they can look for that growth. Yeah, they can throw headcount at it and they can say, “Okay, let’s hire 50 more salespeople.” Or they can say, “Well, what else can we do to extract greater effectiveness, greater sales productivity, and greater outcomes from the existing resources by rethinking process improvements, workflows, handoffs, and any other areas of friction that are preventing the business from running smoothly?”

And so, that’s always been a place where I’ve been a nerd. I mean, just that simple. And it started out from just being a member of sales teams, so it wasn’t with any like real formal authority. As a member of sales teams, I can remember super early on when I was working at a company called Matomy, I was on a great sales team. We had a lot of fun, a lot of laughs, a lot of competitions that we would just create for ourselves and silly jokes and things like that, but we also had some areas of friction in being able to get our work done. And those were things that interested me. Like, hey, if I’m experiencing this area of friction and it’s causing me a little bit of frustration, how can I solve this, not just for myself, but for our team?

And so I would look for ways that I could hack little improvements to our CRM, so that we wouldn’t have to enter data like 500 times. Or that we would have more dependencies of data, so if I said A, then the dropdown menu would have B, C, and D choices, and I wouldn’t have to kind of reenter things. But one notable process was around the financial part of getting a deal done, so we worked on a pro forma basis where clients would prepay us. We were in the AdTech space and clients were essentially prepaying for some of the advertising and marketing solutions that we were going to provide.

And we were based out of Tel Aviv, so we were operating globally, and we needed to secure these prepayments from clients all over the world, which could really derail the deal momentum. You’ve built up this momentum, you’ve got the sales cycle in a certain place. You’ve finally got the contract signed, and then you’re just sitting there waiting for a prepayment to come through. And it can be a matter of two days, but it could also be a matter of two weeks. And in that time, it could kind of bring things to a screeching halt and that felt unnecessary.

So around that time, I reached out to a buddy of mine, or somebody who became a buddy of mine in the finance department, and really tried to understand, okay, what were the critical components that he needed in order to run a really smooth accounts receivable process? And then how could we multi-track that? So rather than having things run sequentially in our sales process, which of those things could we pull forward and start to run on parallel paths so that we could get to the finish line pretty much at the same time without slowing down the deal? And that was just one really great accomplishment where we were able to shorten our sales cycles, reduce some of that friction, but also build some cross-functional bridges, which ultimately helped us over time.

The Importance of Deal Momentum

Barry: Absolutely. Let’s even talk about that a little bit more. How important was momentum to the deal? Did you see a difference before and after once that solution was solved?

Natalie: Yeah. We were getting deals moving and into integration. Prior to that change, we typically saw like a two to three-week delay between contract signing to launching of a new client’s program. We were able to shorten that to under a week, and in some cases, even less than half a week. And so, the benefit there was that we got the clients excited, rightly so because the solutions that we were going to deliver were going to be fantastic for them. But we retained that excitement through the contract signing process and some of the administrative work and moved them with that enthusiasm and excitement into the handoff, into the conversations with our account management team, and really kept that momentum going.

They were much more engaged in that process versus having gone through the boring and administrative stuff, which can really derail any deal, right? Nobody loves to be in the minutia of, “Wait, did you get the contract? Wait, did you send the invoice? Wait, did your finance team get it? Wait, can you follow those things up?” Today, there are so many solutions that can one-stop shop that whole process with the click of a button. And I think DealHub is probably among some of those great solutions. But at the time, we were really just figuring it out as we went. We had a large organization that was operating across multiple channels, multiple countries around the globe. And this was just an overlooked area of delay that once we solved it, really accelerated our path to impact with our clients and kept a lot of team enthusiasm as well.

Solving Revenue Operations Challenges Pays Dividends

Barry: Back to the processes. How did you justify to yourself as a salesperson to not do something that wasn’t going to bring in revenue the next minute? Was that something that you had to deal with? Or we talked before about imposter syndrome, was that a sales syndrome that you had to deal with doing something productive for the company, but maybe not as productive for your paycheck the next day?

Natalie: That is such a great question. Again, I think this changes. I think the narrative around this is changing, and I think that’s a welcome change. My personal experience was just having to do both at an excellent level. It was like the table stakes needed to be hitting quota. I was never going to put myself or my company in the situation of having to have a conversation around the fact that, “Well, I didn’t hit quota, but I improved the process.” I just wasn’t going to have that conversation.

So, my approach was being stellar and making sure I was delivering on my revenue commitments to the organization, whether those were personal commitments or later when I was managing a team and managing a department. We were on our numbers, but these were things that I would just do above and beyond because, A, I was curious about them. B, I had a knack for them. And C, I did know that those would pay dividends over time.

When you have salespeople who are experiencing a point of friction in every single sales process again and again and again and again, and that’s embedded into how they’re going to sell, that’s going to erode motivation over time. And it’s a little erosion, it’s just like a little thing. But if you, as a sales leader, can identify those little points of friction and remove them, your team is going to be able to operate much more smoothly. And that frees them up to start to also think about how they can solve some organizational challenges, or how they can add value beyond just the minutiae of getting this specific deal that they’re working on.

So, the added benefit is that this really has a network effect. You solve this little thing, its effect compounds because now every single time we go through a deal cycle, you will have solved that. And that’s time and energy that you give back to the Sales team to do better and more productive things.

Friction Points in Sales

Barry: That makes a lot of sense. I’m sure every manager or CEO wants a person who does that. To hit numbers and go above and beyond, sounds like a dream. That’s great. What were some other processes or points of inertia that you saw when on the sales team? What were two or three other points that you saw in your career?

Natalie: I think a really notable one, so two other points that are pretty common for having friction can be around new hire ramp-up and also around sales to Client Success handoffs. Those are things that they’re easier to detect because I tend to see them in a lot of organizations as these areas of, okay, if we can get this done better, there’s a real material benefit for the organization that we can have in the short term.

So when we think about the new hire, onboarding, and ramp-up, essentially until those new hires are standing on their own two feet and independently running their own sales or running their own work responsibilities, there’s some cost for the organization. They’re an investment that the organization’s making in some future value that the organization’s hoping to realize.

So the shorter you can make that payback time, the sooner you can ramp people up into their roles with confidence, which is not just about subject matter expertise, but it’s also about navigating the organization. There’s going to be questions or areas that they may not know in the future, but how can you teach them in their first weeks and months on the job how to find answers, how to work well with other stakeholders in the organization so that they can continue to build on their knowledge and expertise.

Solving that can be really impactful for the organization. That’s kind of one big area that I’ve focused on. Every organization that I’ve worked at, I’ve left this onboarding and training guide that’s typically been adopted, either department or company-wide, by the time that I’ve left because we see that people are embraced really well into the organization, ramp-up into their roles with confidence, and become really embedded members of the community, which I think is the goal.

And then the other area of focus has really been on that client success handoff. So when you spend X many months working on a deal, learning about the client’s business case, understanding what the client needs, what kind of value you’re hoping to realize from the product, and ultimately building that relationship with them, what you want to be able to do is transition that very effectively to Client Success. And if there’s any breakdown in that, that can be super damaging. So finding ways to make that smoother, faster, more effective, and have a really great knowledge transfer are things that I’ve put in place as well.

What is Salesperson Ramp-Up Time?

Barry: I think both are very critical. With regards to ramp-up time, something I’ve been wondering recently, I’ve been seeing KPIs, “Oh, this will help you ramp-up sales reps in six months.” Or, that’s the benchmark. And, “This will help you increase ramp-up time by 50%.” There are some interesting numbers. What is the ramp-up time? How do you know when your sales rep is ramped after they’re hired?

Natalie: Wow, that’s a great question. It’s going to look different at every organization, and it’s going to depend a lot on what those cycles look like. So if you think about a company that’s running much more transactional, shorter sales cycles, I think that ramp-up can tend to be faster because you can practice all the parts of your sales cycle much more quickly, much more frequently.

But if you extend that sales cycle and you’re working in scenarios, the majority of my experience has been with sales cycles that have been anywhere, let’s say, on average, from three to four months with, of course, outliers much shorter and much, much, much longer than that. But let’s say three, four-month sales cycles, you need to have your salesperson, who’s ramping-up, practice with expertise every single part of that sales cycle enough times that they can make mistakes and enough times that they can actually do it well.

I think managers tend to underestimate how long it takes for people to actually ramp up. But I think if you can think about that, what you want to do is present them with the opportunity to make mistakes, have them make some mistakes early on in a low-stakes situation. And then, ensure that you’re shadowing them while they effectively manage later stage parts of a deal, negotiations of a contract, the process of handing off into the organization and do those with some guidance and shadowing. If you can do those, again, on parallel tracks, rather than waiting for it all to happen sequentially on their own self-generated pipeline, then you can really accelerate ramp-up.

What can that look like? It can mean that you can actually have them take over some mid-stage deals even before they’ve “earned it,” but just so that they can practice managing the second half of a sales cycle much earlier on than it would naturally occur. Or you can have them shadow you in some other high-stake situations so that they see what it’s like and you do a lot of debriefing after every client call so that you can talk through, “What did you think? What did you notice? Did anything surprise you? Did you have any questions? Is there anything that you would do differently?” And make sure that they’re getting that opportunity to envision what success looks like on later stage parts of the cycle?

I think those are just some tips, but again, how do you know that somebody’s ready? You’ll see it, you’ll see it when they’re ready. Some good tools that I’ve used along the way have been these 30, 60, 90-day ramp-up plans. Where at the front end of somebody’s joining the organization, you already identify what are the things that you and the organization are committing to providing them within the first 30, 60, 90 days, and what are the commitments or deliverables or milestones that they need to hit in return? And that’s a little bit of this contract that we make with one another. They’re accountable for hitting those milestones. They’re accountable for being able to deliver on certain competencies, certain behaviors, certain soft metrics, as well as hard metrics, at each of those timeframes. And if people are following that plan, then they’re on their way to ramping-up successfully.

A Smooth Handoff From Sales to Customer Success

Barry: That’s super interesting. And I think for season three, we’ll do a podcast on ramping up sales because we could go even deeper. You have a lot of these tips I think would be really good for our listeners. Give us some tips from the sale to the Client Success/Customer Success, that part. One thing I was particularly interested in is how much time the Sales rep has to educate Customer Success, whether that be time writing notes and sales boards, or time just being on a phone call or a time making an introduction with everyone on the call during customer onboarding. Would love to hear some tips on improving the customer experience during the handoff from customer acquisition to onboarding.

Natalie: Again, I would say there’s no one-size-fits-all. I think, as an organization, you have to figure out what you need, what your clients ultimately need in order to feel supported and to feel that you haven’t wasted their time and that you’re not asking them to repeat pieces of information that they’ve already shared with you or that you don’t act as though you’ve misplaced key parts of the information that mattered to them.

So for the client, we want them to feel supported. We want it to feel seamless. We don’t want it to feel labor-intensive, right? So, we want it to be super, super easy. That means that a lot of the work and coordination need to happen behind the scenes. And again, thinking about that anecdote that I shared with you in the past about that finance piece. What we want to do is see if it takes a while to figure out who’s going to be the account manager, let’s say you’re not working in pods, so there might be a little bit of a question mark. Like, “Okay, should Anne or Joe or Barry take this next account?” If that’s a decision that needs to get made, how can we front-load that decision so that we’re not waiting until everything is ready to start asking the questions? So, we can start to run things parallel as well.

And then, consider what’s the information that Client Success needs in order to be able to step into this account and really get the client to realize impact as quickly as possible. So they need to understand, who’s who? They need to understand the power dynamics. They need to understand, what are the expectations of the client? What are they looking for out of this engagement? We need to understand what’s the status quo? We need to understand all the relevant metrics that we’ve heard from the client.

So in the case of different marketing technology solutions that I’ve sold in the past, it’s what’s the volume that the client has going on today? What are the conversion rates they’ve got going on today? What would ROI mean for them? How are they assessing ROI? How quickly can they assess it? What platforms, what tools are they using? Right? So getting that, all that stuff that we’ve diagnosed early on, making sure that all that information is available to our Client Success team.

And you asked around how much time and where they are documenting and all of that. I like the idea of trying to put those pieces on the path of work, so rather than having it be this disjointed event where Sales all of a sudden sits down to write a whole handoff, which sometimes can happen and it can be okay, to embed it inside the CRM so that while they’re on the path of making this deal happen, as they learn the stats, as they learn the critical information, there’s a dedicated place where they can already jot down those notes. And by the end of the deal cycle, they’ll have populated probably 85, 90% already of all the information that they’re going to need on that handoff document, and then they’ve just got to put finishing touches on it.

What we built at PX, which was great, was a bit of automation into that as well. So information that they put in one part of the CRM would automatically pull into the handoff template. And then once they actually filled out the rest of the handoff template with all the other questions that needed to be answered, with a click of the button they could submit it, and that would get sent out to the head of Client Success, the Client Success team. And we could already start that dialogue around what questions do people have, who’s the best suited to manage the account, and how can we kind of get things on the calendar already?

Barry: That’s an interesting approach to customer success and definitely impactful. I started off this podcast saying that we talked about 10 things. I think now we talked about 20 things. We could do a whole season just of Natalie, so this was great. Thanks a lot for joining us on this podcast. If people have any questions, where can they reach you?

Natalie: First off, thanks so much. This was a lot of fun and really, really great chatting with you about all this stuff that I love nerding out about. Best way for people to reach out is on LinkedIn. You can find me there, Natalie Peled David, and I’m happy to chat, talk about all things go-to-market, revenue operations, sales, leadership, or the transition from sales to all revenue leadership, and really happy to talk about these topics in more depth.