
SaaStr 782: How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer Former Head of Revenue at and Americas leader recently joined us to share her insights on one of the most critical roles in any SaaS...
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Welcome to the official Saster Podcast where.
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You can hear some of the best Saster speakers.
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This is where the cloud meets up.
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Today on the Saster Podcast, so you.
C
Can probably get a sense for what the flip side is on the talent side, if you're trading people out quickly, I've certainly seen this before. If you're not ramping people effectively, that's a real sunk cost. Customers feel it when reps don't know Product Jason, I'm pretty sure this is something that you opined on time and again in many of your posts. It's just the importance of actually knowing the product and if a manager is not there to enable and reinforce that positioning when to go for the enterprise sku? When to go for the pro sku? You need the manager to be listening and on those calls and analyzing the conversational intelligence to know if the quality of the conversations is there.
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Hey everybody, thanks to the 10,000 of you who came out to Saster Annual this year.
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We had a blast and big news.
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We'll be back in May of 2025 or in May of next year. That's right, SAS train will be a bit earlier next year. The 13th to 15th of May 2025. We'll still be back at the same venue in the SF barrier in our 40 acre San Mateo County Event center campus. And tickets are never cheaper than right now. So grab your tickets@saster annual.com with my code Jason50 for an extra discount on our very very best Jason50@saster annual.com see you next May at Saster 2025.
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Hey.
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C
Awesome. Thank you for having me, Millie and Jason. I'm happy to be here. I've been at my new role for only eight days now, but I'm working for Francisco Partners Consulting, which is an arm of Francisco Partners, which is a private equity firm based out of the Bay Area and it's an interesting pivot for me. I really love the kind of work that I did. I've been a revenue leader forever.
B
Just a meta question before we I really want to save the time for talking about frontline sales managers, but HubSpot to Bill Hub and I may have this a Little bit wrong. But HubSpot we're talking about there's bigger customers but 10k, 11k, 12k customers on average. The M and SMB as Brian used to say or likes to say. Right. Bill's got a lot of tiny customers. Yes, tiny. I don't know what the average ACV is but it might be 1k or something like that on average. So if you had to summarize all the differences between selling to 10k and 1k, what resonates with you? What are your big, how different are they? What are the biggest differences that come to mind?
C
Yeah, great question and I'll tell you a lot of pattern recognition between the two businesses. Jason HubSpot when they opened the aperture to go to a freemium motion we got a lot of those lower end of the market customers. And so I think and to be honest, the pattern recognition even extends back to when I was at LogMeIn which had the product join me. It had rescue it. They merged with GoToMeeting, became GoTo. But I think any company that is working in that micro small business space really has to delineate where do we put resources and investment and how do we create more of a PLG motion in order to continue to create that moat and that volume and improve those conversion rates down market in order to free up time, resources, space to really capture if it's lower mid market, if it's really the upper end of small business. But how do you segment and make sure that you have the right go to market motions across marketing, sales, execution and customer success. So similar. When I started at HubSpot I ran the small business sales team for two years there. A lot of our customers were below 10 employees. So yeah, similar. Different but similar.
B
And just one last follow up and then I'll then let's do frontline sales managers and ask more questions at the end. But if you had to summarize today there's been inflation, the world has changed.
C
Yeah.
B
Where is the line where you can have human in the loop in sales and when you just can't? When can you Afford it in 2025 what's the line you think if you had to, if you had to draw one at an exact acv?
C
Oh, that's a good question. I would have to say it depends on where the company is in their growth trajectory and where you are in your learning curve about your ICP. And if you know your ICP down pat a 5k ACV and below I would 100% try to figure out how do you get as much of an, of an automated process to engage. Yeah, that, that would be my, that would be my perspective.
B
Yeah, it's good. Cool. 5k is a great one. Okay, let's, let's talk about frontline sales managers. I could ask you a lot of other, I could ask you other questions later, another time, but this is great. Thanks. Thanks for kicking it off.
C
Yeah, yeah, you got it. So listen, Jason, you, you pinged me. I think I had a post of some kind on, on LinkedIn. I usually do this while I'm waiting in line. My LinkedIn post @tate, which is my coffee shop nearby, and, and you said, hey, let's chat about this on Zaster. And frontline sales manager, I've run the full revenue organization at bill was1.3 billion in revenue publicly traded company. I had about 500 people under me. At HubSpot, I was head of revenue for the Americas. I had about 800 people over me. But I have a real special place in my heart for the impact that frontline sales managers have. And I have to say, and this is from my own experience as we take a look at the invest investment constriction that we've all had to endure over these last few years, one of the first areas that we decided to not invest, which to be honest, I think was a mistake by we also me in terms of prioritization was in frontline manager enablement and it. There's real impact. So what I'm going to walk you through today is lessons learned from my own perspective and where not in investing in the strength of the frontline sales managers, where that can have downstream impact into the business and some best practices that I've learned along the way. So let's get into it. Why are frontline managers so important? So listen, I'll tell you. I go into almost every new fiscal year, some of you that's gonna start January 1st. For others it will be other times. And I always go in with this glass half full excitement that this year is gonna be different. We have the right strategy in place, we have the right goals in place. We're gonna execute better than we ever have. I'm signing up for higher sales productivity because we're gonna implement these new tools and I'm always so excited as I move into the new year. But as you actually practice and go through the motions of achieving your goals, it's the tactics that can fall short. Sure, the strategy can fall short. But every single year any company I've been at, you start with the mission. This One's usually pretty fixed. You have the vision, whether it's for the year or the next few years, then you have what are the overall objectives, the strategy that we're going to take. And in the end it's the tactics. And when we take a look at the frontline sales managers, this is a group that is responsible for delivering and executing against the tactics in order to reach your goals and your overall strategy for the year. And I'll tell you, this can fall short. And for me, I had at HubSpot, for example, over a hundred frontline sales managers under me. And what's great about high volume sales and large teams like this, again, is that kind of pattern recognition. And so when I looked at what are some teams that are doing things really well, what are some teams that aren't, a lot of it came down to the manager. And what I saw was everything from one manager's team sold more of our enterprise SKUs. One manager's team had super high volume, but it was low ACV and they missed their number a bunch. Another one might be that one manager kept churning reps out. And so you start to see at scale where some of your tactics that you thought you just execute against fall short if you don't have the foundational strength of your frontline sales managers. So in my view, this is what the benefit really is when you take a look at not just the impact of a sales manager to their team, but the impact that it can have within the organization. First and foremost, they are hiring your next gen of top talent. And ideally they are hiring the next managers, the next directors. And you really need to get that hiring playbook really tight and ensure that your frontline managers are doing a great job with their interviewing and who they're bringing on board and that you're measuring the impact. We actually did a really interesting study when I was at HubSpot with a graduate student from mit and this was actually Brian Halligan, the founder had asked us to do this research, which was if we take a look at how we scored our hires, we had scorecards for everyone. We had characteristics and attributes that we were hiring on, we would give them a score of 1 to 5. We took a look at those scorecards and we looked at the attainment of those hires 12 months after they were on board, 18 months, 24 months, is there anything we could glean from who we hired and what they scored highly on that translated to really top performers? And the number one aspect was coachability. And so I share that with you because Ensuring that your frontline managers are hiring well and that you're going back and looking at their track record. Are there people who are treated too early? Are there people who they were just low performers, they weren't ramping on time. It's the frontline manager who really is the key to the success of all of that headcount in your revenue organization. That's one of them. The other one is the sales manager by proxy of overseeing a team of 7, 8, 9, 10 reps. They have acute pulse of the customer as well as the macroeconomic environment. Give you a quick example in early 2022, this is when you started to on the earnings calls of Salesforce and and many others. This was the beginning of the sales pipeline halt. Right? We had the post Covid boom and then it came to a bit of a halt. And what we started to hear from reps, but managers who were sharing this up is the CFO is now on the decision committee. We have to go to the PE firm or the board for approval. We started to see that the financial buyer was a much, much more important key stakeholder. The point here is the customer, the access to the customer. You're going to first hear that from the reps and the manager. And so they play a really key role of listening to prospect and customer sentiment process. They have acute awareness of what's working and what's not. One of the things that just came off a call with a bunch of portfolio companies. One of the things we were talking about is the importance of data strategy. And with that data strategy managers and reps, they're going to be the first ones to tell you we have bad data, we have duplicate data. There's one rep who's working at the same account that I am, the customer, the prospect, they're not happy about it. Managers are the first ones to point out there are problems in our overall process. They can be a real key into making sure you're building for the success of the long term. Of course they enable people, they're coaches, dare I say, they're armchair psychologists. They are mentors. But they also are teaching the product positioning, pricing positioning. They're teaching the systems, they're teaching the reps about the icp. Now of course, great companies have this through an enablement department. But the person who reinforces it and also makes sure that their reps are executing on what they've learned as effectively as possible. That person's the frontline sales manager. Of course, the revenue drivers, they're the key to growing product acquisition Expansion, retention and especially when you're rolling out a new product and or go to market strategy for whether it's product expansion, if it is managing your current customer base, you want to make sure that your managers are in lockstep on the how and if it's not working, that you're getting that feedback as soon as possible. So of course that's a big one. And then finally culture. I know everybody has heard this. People quit their man at their boss, not their company. I think that's a half truth, but it's true. Bad managers, you're going to read it all over Glassdoor and if you're not investing in them, that's going to lead to poor performance for the reps, that's going to lead to poor culture. And one of the things that I've seen very consistently in terms of being one of the biggest growth drivers at companies I've worked at, it's having highly tenured reps. Those reps are the ones that tend to have, in my experience, tend to have the highest in rep productivity. So you want to retain, you want to hire right, you want to retain those reps. And when you have the right leaders in place, they want to stick around and they drive higher productivity. So I would say tell your cfo, investing in the, in the above is worth the consistent investment. So you can probably get a sense for what the flip side is on the talent side if you're trading people out quickly. I've certainly seen this before. If you're not ramping people effectively, that's a real sunk cost. Customers feel it when reps don't know product. Jason, I'm pretty sure this is something that you've opined on time and again in many of your posts. It's just the importance of actually knowing the product and if a manager is not there to enable and reinforce that positioning. When to go for the enterprise sku when to go for the pro sku. Do you sell multiple products upfront or do you do a single product that you land with, then you expand within the first 90 or 100 days. You need the manager to be listening and on those calls and analyzing the conversational intelligence to know if the quality of the conversations is there. So this is really important. As I mentioned, from prospect perspective, problems will multiply if you're. If they don't get addressed. Managers are the ones that are bringing those forward, often loudly and then of course missed revenue goals, long tail of underperformance. And we already talked about the impact to overall culture. Listen, the impact of this really is sunk cost. And please take this as a warning from me. I would say at various points when budgets were tight, the prioritization in my view is always enabling the reps, right? Even if there was investment in evergreen content. But if you are not investing in the managers to ensure that they can reinforce there can be a real gap there and it will be a hit to not just your revenue but also to your overall investment strategy into your revenue team. How can you build a world class frontline manager team? So this is, this is a lot here on the left. But as I was thinking about this, I really think there were three components, maybe four truly that play into really building an effective team. The first one is consistent learning. We're going to talk about, you know, what that can look like both from like great investment there and or piecing it together. It doesn't have to be super expensive. It just needs purpose. The other one is measurement. Measurement all day long, everything. And I would say the bias for most companies is to measure reps who are underneath a manager. We're going to talk about how you can actually measure a manager and their effectiveness. It really packs a punch. And I've seen that if you measure the right things in managers against managers in the way that you measure, that can really elevate the entire group. So measurement's a big one and then of course culture. So we'll, we'll go into a bunch of these. A few I want to call out here on the left. Expectation setting I think is a big one and there's never a wrong time to get this started. But really making sure that you're purposeful in spelling out what is the expectation of a manager, what is the expectation of a rep and having that written down for everyone to access and sign off on. And this, you might iterate on this once a quarter, twice a year, but making sure there are clear expectations of what you expect of your managers. Repeatable, scalable frameworks. If you can make things easy. I'll give you an example. We just, I did a training when I was at Bill with all of our managers and Mike Weinberg. I don't know if any of you on the call are familiar with him. Highly recommend him. He did training for us. He did it at HubSpot as well. He has a super easy framework about pipeline analysis. It's called RPA and its results Pipeline activity. And it's just letting the reps know once a week we're going to have a call. That's all we're going over what are your results, what are your pipeline, what's your activity? It's a super easy, quick framework. The more that I think you can have quick, easy frameworks that you can scale, I think, I think the better. A culture of coaching I think is a big one. This is another one. Different companies have different perspectives on this. Some think the sales manager should be responsible for pipeline management and ensuring that they're in deal coaching. The other one is coaching on deal strategy. It's on how do you expand your average deal size, how do you sell multi products up front versus maybe just one product up front. A manager really needs to analyze the tea leaves of what's happening on a rep by rep basis and serve as a coach to help them improve their performance. The difference between good managers and great managers is good managers say this is what you were doing. Great managers say this is how you can do it better. And it's the how that makes a real difference. Manager career pathing. This kind of falls into that learning bucket. Does a manager know what they need to do in order to promote? And that's one of the things I did love about my time at HubSpot is we had automatic promotions and so people were gunning to hit the numbers that they needed to hit in order to get promoted. So I thought that was a great one. And of course you need to make sure that the manager is aligned with the company mission, vision, strategy and goal. For those of you on the call who have worked in revenue, many of you know when you're know that certain managers are not aligned with the goals for the year, they're not aligned with the strategy and if their friends who are managers know it, you have to imagine the reps know it as well. So how do you make sure that everyone is singing from the same PIM sheet? Okay, so this is on the the setting expectations early. I just wanted to break this down on the align alignment. Um, let's actually start at the bottom here. I actually have this kind of numbered out of whack. But nonetheless it all starts with the company goals, right? Does everyone know what we're going towards? Clear understanding and ability to articulate the why behind the company goals. The director and or the vp, our head of sales should make sure that all of the managers can articulate back what are the company goals for this year and why? Why do they matter? So I think that's actually a really good exercise culture and values. Is this person culturally additive? Are they demonstrating high expectations for the highest of standards? How do you know that I mentioned this earlier, but really that clear expectation setting a guidebook for the manager role. What are their responsibilities? What does success look like? I think in too many organizations, manager success means they hit their number or they didn't hit their number and that is very rudimentary. And so there should really be some strong success criteria around that. And then what does it look like if they were progressing from a softer skill and, or they have mastery? I think there should be different measurements that they are aware of that happen on a weekly basis, monthly basis, quarterly basis. And some of those measurements should be qualitative and some of them quantitative and ideally benchmarked against their, their, their management set. If you have multiple managers. And then finally is there a consistent feedback loop? Is there a coaching culture to coach that frontline manager? What does that look like? What does that sound like? And do you have that in place for your organization today? So I think that's a, that's another really important one. So on the learning front, I think there's a lot of areas where you can strengthen manager effectiveness really easily. I really loved when we did, I went through, we did a transition of what our pitch was at HubSpot and everyone in the company on the revenue side, head of sales, every SVP had to record themselves giving the new pitch and you needed to be certified and you had a panel who listened and they gave you a score and they gave you feedback. Managers should go through this too. And at the top of the call, one of the things I had mentioned was sometimes we really push rep enablement and the managers don't have to go through these certifications or these trainings highly recommend that there's a level of rigor and you make sure that not only can your man have they gone through the certification, but they can prove out that they can execute it really well and they have an execution plan with their team. Situational leadership. Lots of companies do this through the HR organization sales methodology. Some of them like Sandler or like mine, Mike Weinberg, who his is on manager effectiveness, they incorporate manager training in that. But I think sales methodology training, I don't care who you are doing it once a year is helpful to absolutely everybody. There are always new tips and tricks on how to be more effective in the way that you engage and converse with others. I think this one of them holding effective one on ones. And I mentioned frameworks, there are a lot of them out there. If you just Google effective one on ones. There's a whole science behind how do you listen more. What's the difference between telling and guiding. How do you agree on next steps? Action items. What are those deliverables? What's the method in which you track your one on ones? I think a lot of frontline sales managers, especially if it's the first time they're doing it, they struggle with being liked versus being effective. And a lot of one on ones, you know, don't get recorded or they're only recorded if someone's not doing well. I think the practice of effective one on ones is a really good one that I don't care what department you're in is really good. One that is really inexpensive, that I know my teams have loved in the past is when you bring in the CFO to talk about trends in the business, why the stock price might be going well, why it may not be going well, what are we hearing from investors? What role do they play in it? There are all sorts of ways that teams can figure out how they can get closer to the macroeconomic trends that are happening. And then some of these other ones, Diversity bias training. These are always really great food for thought as you think about building inclusive and diverse teams. And of course radical candor. I think this is an area that I have seen managers struggle with, especially when they become close to their team and they've managed some people for many years. Those are the reps that they tend to not get a lot of feedback or if they're one of the best reps, their learning can end at times with their manager. And so making sure that there is this continuous feedback loop that managers have the strength in delivering. Radical candor. To tell someone the path you're on is not the right one. Let's get you on the right path, I think is really important. And then these last two, I think any, anyone who's manager level, even director level at companies, how do you influence with that authority within the company and or how do you effectively manage stakeholders internally and execute change? My hope is so many of your businesses are high change organizations because that means that you're growing and these are all areas in which you can, you can enable and improve your managers. This is the area that I geek out and makes me feel like I have real handle on what's going on in my business. This is the measurement side, right? So effective measurement is really effective management. So I would really implore you to think about how you analyze the impact of a frontline sales manager. So I talked about this before. Daily, weekly, monthly, quarterly manager goals. Both companies, last few companies I've worked for culture Score actually having a manager employee net promoter score tells you a lot about how the team is feeling and where the manager's effective. If you don't have that in place at your company Now a very simple Google form that says what is Jason good at? What should Jason continue doing? What should Jason stop doing? Any other advice you'd have for Jason? Really easy way just to get some very quick feedback from the team. This one I really love. When I left Bill this is an area that we really started to measure. But of the managers we pulled this from GONG data. How many calls are they attending? How many calls have they scored? How many calls have they listened to? That really goes to show coaching and engagement with coaching and the reps. We actually did an analysis when I was at HubSpot and we saw that the managers who engaged most in GONG had the highest attainment. And then lastly on the measurement side, just an area I recommend is a manager benchmark scorecard. This one right here, this first bullet is one of my absolute favorite ways to measure manager impact and effectiveness. What percent of their reps? And you can do this for last month. Trailing three months, trailing six months, trailing 12 months. What percent or above? A hundred percent? 1 10? 90 to 180 to 90 below that. That in my view really gives you a good sense of what is the balance of strength of a manager. And you'll have a manager who is crushing their number. They have a great territory, they inherited some of the best reps but they really have two reps carrying them that have been banner reps for years and years. So when you take a look at the balance of health of a team, I will take a manager that you know is bringing people up and over a hundred percent more of them than the manager who's crushed in the number. But it's only from two people cause that's high risk. So I really love that measurement repetition. This is another one. You see a manager is attrited maybe three reps over the last four months, five months. You're going to think there might be something here. Overall rep productivity. How does that benchmark against some of the other manager teams? The amount of ramp time is the manager making sure that they're getting the reps up and running quickly. And then the commercials. What is their acv? What's their product mix? What skus are they selling? How much is their discount? I've seen a lot of variants with manager discounts. Sales cycle length. It's really interesting when you have so many managers at scale and this pattern Recognition that you see a lot of this differs manager by manager. And it's not just reps. You see the change. And so a lot of this really is behavior that can be worked on and improved. And then this last one, which I think is certainly important for anyone who is a revenue leader or CEO, you want to make sure you have forecast accuracy. And so measuring that on a monthly basis, how accurate is the manager's forecast? What is the variance? Is it plus or minus 5%? The ideal for me has always been within about 3 percentage point 2 is really ideal. But that forecast accuracy is really important. And then we're getting towards the end here. But I mentioned this before, direct managers are often the number one reason employees stay or leave. A best practice that I've seen with my teams is you start a new year having everyone on the team under a manager together. Define what should our team culture be, what should our team identity be? And spending the time to talk about where are we, how do we want to operate together, what are our guiding principles, and what do we want to hold ourselves to? Making sure that the company values are really permeated through everything the team is doing. And examples of that should be celebrated often, for example, humility or accountability. I think those are great ways to showcase, you know, once a month someone gets a values award. Team meetings. I've. I've certainly joined some snoozers of team meetings. They should really be to energize and align. And in an interview process, I would specifically ask frontline managers who are applying, what does a great team meeting look like to you? How do you galvanize your team? What do you do? What do you learn? What do you bring to the table? Transparency, candor, high execution, psych. Safety, of course, is important and just reinforcing the fact that managers really are that connection point from the company culture to the team culture. And we all know that unfortunately, certain people can get it wrong. And that makes a real big impact. And that one Manager can impact 7, 8, 9, 10 people, which certainly is a hit to, to the culture. Okay, real quick, internal versus external hires. This is a question I get a lot. And, and I think they're both great internal hires. It's gotta be faster ramp time. It certainly bolsters the culture when it comes to reps and other managers seeing career progression. And that institutional knowledge at a company expands. Right. There is a real immediacy to the impact that an internal hire can have. That said, at a certain size and scale, you want people who have seen the film and can add new value, new perspective, new skills to the team. And if you're taking a look at your team and almost everybody there has grown up at the company, you might want to think about bringing a fresh perspective on how things can be looked at and executed differently. The second bullet here is especially for those disgruntled managers who are over the baggage of systems issues, data issues, process issues, bringing in someone fresh who can see everything from fresh eyes and being grateful to be at this new company with eyes wide open. I think that can also bring a real boost to other people around them. So they're both good needed for different times of growth. Common mistakes this one I mentioned investing in rep development and assuming that manager development can be lumped together, lack of a consistent feedback loop on the manager's performance beyond hitting their number, looking at manager attainment simply as a number, not as a holistic scorecard. And then the success criteria of what really solid effective good manager looks like not being codified, whether it's through the expectation setting or during review periods. But some of the things that should be brought into view include are they effective at cross functional collaboration or do people that they work with hate them, do they manage change well or their team laggards with change or do they take change very quickly? So final thoughts and tips really make investing in frontline talent a priority and in every year line item as I mentioned there are a lot of inexpensive ways to do it, but it really should become a fabric in the way that you operate having a continuous learning culture. I think you should think about quantify the cost of getting it wrong. There are real costs to the business top line revenue as well as just long term impact. If you don't get this right and I'm happy to discuss some ideas on the many ways to enable and prioritize that outside investment in the short term in order to get that long term roi. That's what I got. Jason hand it to you or Amelia? Yeah, we have two people asking the same question that I think you can vote. We've written about it a lot on faster but I think good to get both of your takes here live which is what do you think is the best sales comp plan structure? It's a very loaded question. I don't, I don't think I can actually give an answer to that. And it's because different companies you might be at one company and it might be all new business logo acquisition. It might be you need to get the deal size higher. There are a lot of variables that play into that and I even on my own team there isn't a one. One size fits all that I've seen. There have been different comp plans for different people but the standard I see for SaaS reps 50% salary, 50% variable. And some companies have it where if the rep hits 110% the company hits a hundred. That's the HubSpot model. Some have it if the company. If the reps hit 90% the company hits a hundred percent. So they're all different. I don't think there's one best answer.
B
What do you think Michelle, on the when you're trying, when you're talking with candidates, base versus ote, what are the flags and versus attainment. Right. Because at the end of the day base if you're any good in sales, even if you're mid pack bass is almost meaningless. Right. It's a tame and ot. What are your thoughts on that? What are your thoughts on candidates that are obsessed about bas? What are your thoughts on the fact that I find most sales folks can't do this math very well.
C
Yeah. Yeah. Can't.
B
They're obsessed. I need the highest OTE. I need 10k more OTE, but it doesn't matter half the time. So thoughts on that mix of that mix of pieces and the ability to explain it to candidates.
C
Yeah, I so I will say in my heart of hearts, I've been in sales now for almost 25 years, 24 years. I have seen so many great reps leave companies, really good solid companies because they got a higher base, higher ote and it never came to fruition. And so I think you're.
B
Yeah. Like never. Right.
C
Never. And your question's a super valid one. And. Or also to chase a title, a big title and they. They're not even ready for that title that is just being given to them. So I would definitely say go to rep view if if they have or glass door depending on the company size. But it's always nice to see if they could talk to another rep or hear from other reps what percent is. Are they actually making their number anything below 50%. I would just be a little wary of just the odds are much lower that you're going to hit your full ote. I would also ask about things like accelerators. I would ask about clawbacks. I would ask about what is your retention. I know that people get excited to get new jobs especially if they're trying to get out of something that they're not happy about. So they'll forego Asking those tough questions, it always bites you in the tush. And so you gotta ask about accelerators, retention, clawbacks, overall rep attainment is my recommendation. Yeah, we bring on Ray, he's got a good question.
B
Sure.
D
Thank you Michelle for the session.
B
It was great.
C
Yeah, you got it. Thanks.
D
Here's my question. How did the so manager to AE ratios while you were at HubSpot and you talked about like the importance of frontline management, what did you find was the ideal manager to AE ratio at HubSpot and how would your answer change if you think about 2021 world and 2025 world going in the next year?
C
Yeah, good question. So I will say the sweet spot, this is my ideal sweet spot, is always seven reps to one manager. Based on where I've worked. I found by the way, that's expensive. That's an expensive model I've found. Even when at HubSpot we were a more of a single product company. So I started there in 2018. The sales product hadn't really busted out just yet. 2018, 2019 is when it really started to get its legs at scale 9, 10 was just a lot and it, and it depends what percent of your reps are you ramping? What is the ramp time? How much enablement does the company invest in? How much does the manager have to do? How many products do the reps have to sell? What is the sales cycle length? And the more complex the sale by nature of sales cycle length is how I would, how I would measure that and number of products is where I would err on fewer, fewer reps per manager in terms of the ratio.7 is a real nice to have. That's a very choice setup. I would say eight to eight. Eight is more likely. Nine I think tends to stretch it.
B
Yeah, good coaching. Cool. This was great. Michelle, thank you very much.
C
Thanks. Thanks everyone.
B
Hey everybody.
A
Thanks to the 10,000 of you who came out to Saster Annual this year.
B
We had a blast and big news.
A
We'll be back in May of 2025 or in May of next year.
B
That's right.
A
SAS train will be a bit earlier next year. The 13th to 15th of May 2025. We'll still be back at the same venue in the SF barrier in our 40 acre San Mateo county event center campus. And tickets are never cheaper than right now, so. So grab your tickets@saster annual.com with my code Jason50 for an extra discount on our very very best pricing. That's Jason50asteraster annual dot com. See you next May at Saster 2025.
Episode: SaaStr 782: How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer
Guest: Michelle Benfer (Former executive at HubSpot and BILL, now with Francisco Partners Consulting)
Host: Jason Lemkin (SaaStr)
Date: December 20, 2024
This episode delves into the critical role of frontline sales managers in SaaS organizations, drawing from Michelle Benfer’s extensive leadership experience at HubSpot, BILL, LogMeIn, and more. The discussion covers how sales leadership and organizational design change as companies scale, core challenges in sales management, best practices for developing frontline sales leaders, and data-driven strategies to elevate team and business performance.
The conversation also tackles pressing questions around comp plans, hiring (internal vs. external), and optimal manager-to-rep ratios in 2025 and beyond.
Why They Matter
Downstream Effects of Poor Manager Enablement
No universal answer—comp structure must align to business needs, not a generic prescription.
“The standard I see for SaaS reps: 50% salary, 50% variable....But there isn’t a one size fits all.” (36:41)
OTE vs. Base Pay
On frontline manager impact:
“They are coaches, dare I say, armchair psychologists. But they also are teaching the product positioning, pricing positioning...” – Michelle Benfer, (09:46)
On when to automate:
“If you know your ICP down pat, a 5k ACV and below I would 100% try to figure out how do you get as much of an automated process to engage.” – Michelle Benfer, (04:50)
On culture:
“People quit their boss, not their company. I think that's a half truth, but it's true. Bad managers—you’re going to read it all over Glassdoor.” – Michelle Benfer, (19:54)
On comp plans:
“I have seen so many great reps leave companies...because they got a higher base, higher OTE—and it never came to fruition.” – Michelle Benfer, (37:38)
On manager measurement:
“I will take a manager that is bringing people up and over a hundred percent more of them, than the manager who’s crushing the number but it’s only from two people, because that’s high risk.” – Michelle Benfer, (32:07)
Recommended for SaaS founders and sales leaders aiming to scale their teams, improve performance, and maximize the impact of sales leadership at every stage.