Welcome to Episode 201! Hannah Willson is the VP of Sales @ Rainforest QA, the on-demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest have raised over $40m in funding from some of the very best in SaaS including the legendary Byron Deeter @ Bessemer, Jason Lemkin @ SaaStr, Marc Benioff himself, Andreesen Horowitz and YC. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper-growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet, prior to their acquisition by Morningstar.

In Today’s Episode We Discuss:

* How Hannah made her way into the world of SaaS and enterprise sales, came to join Zenefits in their heyday and how that led to her move to VP of Sales @ Rainforest.
* How does Hannah think about time allocation and prioritization of time across leads and the sales pipeline? What can AEs do in terms of optimizing their win rate of opportunities? How important a role should discounting play in winning potential leads? Does Hannah optimize for quality or quantity of logos in the early days?
* What does Hannah mean when she says the secret to success is “the calls between the calls?” How do these vary both in content and tone to traditional sales calls? Why must AEs be willing to open up and be vulnerable with leads? What can managers do to engender this? What is the optimal relationship for AEs and product team?
* What does Hannah believe is the right mechanism for feedback delivery? What has worked well for her in the past? Where does Hannah see many today going wrong? What guidelines need to be put in place to ensure this candid and transparent feedback is effective?

Hannah’s 60 Second SaaStr:

* What does Hannah know now that she wishes she had known at the beginning?
* What does Hannah believe embodies good sales rep productivity?
* What is Hannah’s fave SaaS reading material?

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Jason Lemkin
Harry Stebbings
Rainforest QA


Harry Stebbings: We are back in the world of SaaS with the official SaaStr podcast and me Harry Stebbings at hstebbings1996 with two b’s on Instagram. I really would love to see you there, and there you can suggest both guests and questions for future episodes, but to our episode today, I’m focusing really on the lifeblood of any company being sales, and I’m thrilled to welcome Hannah Willson, VP of sales at Rainforest QA. The on demand QA solution that allows companies to discover problems that affect the customer experience before the code hits production. To date, Rainforest has raised over $40 million in funding from some of the very best in SaaS, including the legendary Byron Deeter at Bessemer, Jason Lampkin at SaaStr, Mark Benioff himself, Andreesen Horowitz, and Y Combinator just to name a few. As for Hannah, she has over 10 years of experience leading sales and customer teams at both startups and publicly traded companies including seeing the first hand hyper growth of Zenefits in their heyday and being VP of BD, Sales and Customer Renewals for the western half of the US at HelloWallet prior to their acquisition by Morningstar, and I do want to say a huge thank you to a prior guest on the show, Sam Blond at Brex for the intro to Hannah today. I really do so appreciate that, my friend. But I’m now very thrilled and excited to hand over to Hannah Willson, VP of Sales at Rainforest QA.

Hannah, it is absolutely fantastic to have you on the show. As I just said before the show, I’ve heard so many good things from Fred, Russell, Sam. So thank you so much for joining me today, Hannah.

Hannah Willson: Yeah, thanks for having me. I’ve listened to your podcast for years and Sam has been a great mentor to me so I’m excited we got connected.

Harry Stebbings: Well that is very kind of you to say, but I’d love to kick off today with a little bit about you, Hannah. So tell me, how did you make your way into the world of SaaS and come to be VP of Sales at Rainforest today?

Hannah Willson: Yeah, so it’s a bit of a zigzag, if you will. So I actually started out doing consulting for sales executives at Fortune 500 companies. So that was right out of college. I was working for CEB which is now Gartner and that’s really what got me interested in sales as a profession. From then, I actually rose up the ranks from a revenue perspective in an account manager role. So became a director of account management, then moved over to a VP of sales role for HelloWallet. That company was bought by Morningstar. I then got really intrigued by Zenefits, and so I went there as actually an individual contributor as an account executive. Became a leader there and then came to Rainforest. So I always tell folks on my team that careers don’t have to be linear. You can go to different places. You can do different kinds of things and I think all those experiences have been really beneficial here at Rainforest.

Harry Stebbings: No, I totally agree and I love that kind of folio approach, but I do have to ask. You mentioned Zenefits there, and I’m too intrigued not to. With kind of seeing that hyper scaling first hand, what were some of your biggest takeaways from that experience and maybe how do you think it changed your operating mentality today?

Hannah Willson: Yeah, that’s a great question and we can probably have a whole podcast on that. It was an invaluable experience, I think. I’d primarily been in enterprise sales before I went to Zenefits and Zenefits was such high velocity. So there was so much I got to learn about driving monthly sales cycles and building urgency and building teams quickly. That was certainly invaluable as I came to Rainforest, which is also a high growth environment. I think any time you’re in that situation, of course, there’s challenges as well and one of the challenges of growing so fast, adding so many new customers in different verticals in different size companies is that you often times don’t stop to think about the revenue that you’re adding to the company. So what I mean by that is sometimes it can be a challenge because you’re not thinking strategically about the go to market strategy and is all of that revenue really healthy from a long-term perspective? Will those customers stay with the company? Will they be valuable long-term? So that’s something I definitely think about here at Rainforest as we scale. How do we do so quickly, but how do we make sure that we’re bringing in the right segments of customers that are gonna be healthy for the business long-term.

Harry Stebbings: Can I ask, and I’m too intrigued, does that factor into your thinking? Like is it healthy revenue when your role in a lot of cases is to grow the bottom line in terms of sales and in terms of maintaining those relationships and the customer success and retention side, that’s the customer success team. Is that a siloed approach or is it more of a holistic thinking of is this healthy and sustainable revenue that we’re bringing in?

Hannah Willson: Yeah, I definitely think it’s holistic. I mean from the standpoint of it’s a funnel, right. It starts at the top with the SDRs and the marketing team. It goes down to the sales team and then the customer success team and I think if you’re looking at it in silos, that might not be the most effective strategy for the company and also, as I think about scaling, it’s a lot easier to make mid course corrections or make slight changes to your go to market strategy when you’re at say five million ARR versus 50 or 100.

Harry Stebbings: Yeah. No I totally agree with you there, but I do, Hannah, want to break this show up today into a couple of different elements. I want to first discuss the pipeline itself. I then want to move to the opportunities that sit within the pipeline and then how to convert them and finish on a special kind of superpower of yours. How does that sound?

Hannah Willson: Yeah, sounds great.

Harry Stebbings: Okay, so if we start from the top, we have the sales pipeline where our opportunities sit. How do you think about maybe time allocation and prioritization of leads in the pipeline?

Hannah Willson: Yeah, it’s a good question. I think traditional thinking would say you should always ruthlessly prioritize and focus on those opportunities that have the most likelihood of closing. Obviously, you should do that and I think if you’re in a super high growth environment like Zenefits and there’s tons of leads, that’s definitely really important. That said, I think the best AEs, the ones that are really able to differentiate themselves, the ones that are able to consistently over perform quota are the ones that not only work those best opportunities, but can make things happen with those opportunities where say there’s a 10% chance of closing. Candidly, most of us aren’t in an environment where we’re just flooded with leads and so I think it’s those AEs that can focus on that bottom 10%. Even though there might be a super small chance of them actually moving forward, they can find a way to make a difference with a couple of those, which could be the big differentiator in terms of over performance.

Harry Stebbings: Can I ask, what are the benefits to really focusing on that 10% likelihood of closing leads compared to more traditional thinking?

Hannah Willson: I think the biggest benefit is just quota attainment. So what I’ve always tried to set the tone for our team here at Rainforest and previous teams I’ve led is getting to 90% isn’t good enough and what are those very special things we can do to get to 100%, 120%? That month over month, quarter over quarter.

Harry Stebbings: No, absolutely. You mentioned there really interestingly the element of kind of the best AEs so to speak. So if that’s the strategy and the benefits are kind of clear there in quota attainment. What can the AEs and managers do in terms of maybe optimizing their win rate for these leads?

Hannah Willson: Yeah, it’s a great question and I think it really comes down to how managers deliver or interact with AEs during the deal reviews. So what I mean by that is typically managers will sit down with their team once a week and go through all of their opportunities. I think that’s a good chance for managers to be both positive and skeptical. So I think my team gets tired of me saying this sometimes, but I’ll look at an opportunity which they are so in the weeds with. They don’t think it has any chance of closing and I’ll be like I think we can do it, but I think the AEs are never gonna be as optimistic as the managers are. So it’s our job as managers to help AEs, give them the confidence to believe that we can close these really hard opportunities. But that’s definitely not blind optimism or positivity. I think then you have to balance it with asking really hard questions about every single opportunity and really digging in and understanding every single risk.

One of the questions I love to ask during deal reviews is if you get on the call and the customer comes to the call and they say I love your product but we’re just not gonna move forward, what would their reason be and have them verbalize how they would respond to that. So they’re practicing in the moment. So it’s this very careful balance between being really positive and optimistic and confident that things can move to the finish line, but also being really clear about what all the risks are and helping AEs navigate each of those risks.

Can I ask, if that’s the right kind of structure and communication part of it between manager and the AE to really optimize, are there ways where you’ve maybe seen this go wrong in institutions maybe that you’ve been in or around you in the ecosystem itself where maybe they don’t optimize for this kind of conversion process?

Hannah Willson: Yeah, I think any time you start falling to either side of the spectrum. So any time there is just over confidence about deals and thinking everything is gonna be great and it’s gonna get across the finish line, or on the flip side of that, you go into a conversation and you don’t believe something can close or you don’t believe something can happen, I’m a big believer in the power of positivity and I think you start to set yourself on a negative course if you start to think that that opportunity can never close.

Harry Stebbings: Speaking of kind of opportunities that seem very unattainable, often in the early days I’d speak to early stage startups and they’d say to me, “Harry, we’re never gonna close that named logoed client.” How do you think about kind of the quality versus quantity of logos and the importance of kind of either and where you think about prioritizing?

Hannah Willson: Yeah, it’s a good question, and I think it goes back to what I said earlier on your go to market strategy. I think I’ve been in organizations where we see a good logo and we’re like, oh we just want to bring them on at all costs and we don’t really think about, okay, does this fit with how we now we can best support customers. So obviously that’s not a great strategy for either the company or for the customer that you’re selling to. So I think sometimes it can be exciting when you have a really big logo that is very interested in what you’re selling, but it’s really important to take a step back and think can we effectively support this customer? Will they be successful on our platform given what we know? So in that sense, I think quality often times is more important than quantity.

Harry Stebbings: No, I do agree with you there. You did also say about kind of wanting to get them onboard no matter what. Often with reps kind of one way of doing this is by using discounting as a tool to kind of get opportunities over the line. How do you think about discounting today, Hannah?

Hannah Willson: Yeah, I mean discounting obviously is a great tool in certain situations and it’s something I think most sales organizations will use. I think what you really need to start thinking about is is the discount meaningful for the particular company that I’m working with or is it something else? Because maybe there’s something else that’s more meaningful to the particular prospect or the particular customer that you’re working with. Maybe it’s additional usage or maybe it’s an additional product. So often times there’s more creative things that you can do that will allow you to one, close the deal faster, two, deliver more value to the customer, but three, not sacrifice your ASP.

Harry Stebbings: Yeah, no I love that kind of what drives the decision-making thinking that, but if those are the strategies, in terms of kind of the methods, so to speak, of delivering them, we spoke about some of the strategies there in optimizing the win rates. A common suggestion is always that opportunities are closed on calls. I have to ask, with your many years of experience, would you agree with this accepted wisdom that opportunities are closed on calls?

Hannah Willson: Actually no, and this was something that I picked up a couple years ago from our VP of Sales of Zenefits at the time, Jeff Hazard, and it’s been really game changing for me and I think for Rainforest, which is this concept of calls between the calls. So if you think about it, these standard calls that we do are really formal. You have an agenda, you’ve prepared, you have multiple people on your end. They have multiple people. Everyone has something that they want to achieve out of the call and often times in that very formal setting you don’t get at the real heart of the issue in terms of what the customer’s true needs are, what their hesitations might be, what the risks are that they perceive. So one of the things that we do are these call between the calls. They’re much more informal from the standpoint of you get on the phone with a customer. It’s a one on one conversation. I typically encourage AEs to open it up with some sort of personal conversation and then really start asking questions and trying to get to the heart of the issue.

So maybe that’s preparing for a call that’s coming up. Maybe that’s sharing something that you think is valuable for that particular customer, but it’s amazing to see the things that we hear on those calls and risks that we didn’t even know and objections that we didn’t even realize will come out and often times that’s where the magic happens.

Harry Stebbings: Can I ask, Hannah, what’s the difference in terms of the content that comes out on those calls, the tweener calls versus maybe more formal calls?

Hannah Willson: Yeah, I mean it’s sort of personal. Often times it can be personal risks about moving forward and hesitations that they have and what I always encourage AEs to do is to be more vulnerable. If you are vulnerable about yourself and your life experiences and where you’ve come from and what you’re doing, often times you’ll make a personal human connection with the other person that you’re working with and that can truly be invaluable.

Harry StebbingsI totally agree there on the power of vulnerability. I do have to ask, though, going from the very human and vulnerable element there to maybe a more process driven element, is there a process for doing these tweener calls, be it cadence, be it kind of time between each? How do you think about the right kind of amount so to speak?

Hannah Willson: Yeah, it’s a good question. What I started to do with these calls in the beginning, which was ineffective was just like get on my phone, call someone and strike up a conversation. I think you do need to prepare. I mean there’s obviously been tons of research done that shows that preparation is the key to any effective sales process and it’s the same with these calls. So before you get on the call, you really want to think through what are the questions I’m gonna ask? What value am I gonna deliver to this customer because it’s not enough just to say, “Hey I just wanted to call you and chat.” You know, you have to think of a reason that’s gonna be valuable for them to take a conversation. Maybe it’s something that you forgot to tell them on a previous call. Maybe it’s something that you want to make sure you’re prepared for and they’re prepared for going into the next call with their manager. So it’s really thinking about it like a serious call that you’re preparing for, but then the tone you take is more friendly and less serious.

Harry Stebbings: Yeah, no I do get you. You said there about that tone leading to vulnerability and more personal elements. I’m very intrigued. How does one respond to this from your side, from the sales side and what’s that right communication flow of this maybe more personal information from the customer back into product?

Hannah Willson: Yeah, it’s a good question and I’ve tried the silver bullet here at many organizations. I don’t think there is one, but what we do at Rainforest, which I think is pretty effective, our AEs have a really good relationship with all of our product leaders. This is something the company at Rainforest fosters in terms of communication across teams and whatnot. It is that sort of informal communication where AEs talk to product managers on a regular basis. Obviously they communicate via Slack channels, and a lot of information is shared directly that way back to product. We certainly have a more formalized process too. We have our SE leader who’s very technical lead that and summarize and aggregate what he’s hearing on calls and pass that along in a more structured way to product, but I think it’s sort of that combination of on the ground, one on one conversations over lunch, over Slack, as well as a more formalized process.

Harry Stebbings: Absolutely. In terms of the kind of more formalized process and the flows between the organization there, we had Lars Nielson on the show and he said the best sales engines are velocity engines. I’m really interested. How should it work then, speaking of kind of flows between organizations, how do you think the kind of velocity sales engine should work and maybe be structured to you?

Hannah Willson: Yeah, I mean velocity is huge to me and this is something I didn’t really appreciate, I don’t think, until I got to Zenefits, just in terms of keeping the momentum up. When I think of velocity I think of a sales cycle and the days of, oh I’m gonna have one call this week and another call next week and another call two weeks later, I think are over. I think you need to be in constant communication with your prospects, especially if you’re in a competitive situation because you have to believe that the other AE from that competitive company is talking to them. So I have a really simple way of doing this. I’m sure there’s better ways, but basically when I was an AE I would have a list of all of the customers in my pipeline, whether that be five or fifty, and I would go through it every day and think what have I done for the customer today? Maybe it’s a quick call. Maybe it’s inviting them to an event. Maybe it’s an email. Maybe it’s sending them a t-shirt from your company, whatever it is, but I think that velocity is key and keeping up the momentum is really, really important.

Harry Stebbings: Can I ask, I’ve never actually asked this before but I’m too interested. When you notice a moment of maybe a competitor edging in on something that you want with a client, how does that change the communication, the tone, the cadence of communication? How does that change the situation when you realize that there’s a competitive environment?

Hannah Willson: Yeah, I think it just makes that velocity of communication that much more critical and that much more important. I don’t think that AEs should necessarily do anything different than they would before. Certainly, we don’t want to speak negatively about our competitors. I think there’s things that our competitors do that are really good and can often times be more beneficial for the customer. So we want to be very transparent about that, but I think it does put additional increased need for frequency of communications.

Harry Stebbings: Yeah, no absolutely. Speaking of frequency there, I mean timelines are a super interesting one for me when looking at the velocity engine itself. How long do you think it should go from say lead to MQL to SAL to opportunity and deal? Is there a timeline in your head so to speak?

Hannah Willson: I mean I think it’s gonna be different for every company. I think that some companies it’ll be quicker than others. I don’t really have like a one size fits all approach there.

Harry Stebbings: Speaking of that engine, though, where do you often see it breaking down? Are there common faults or chinks in the armor so to speak of the effectiveness of the engine?

Hannah Willson: Yeah, so I guess I would sort of think about this in two ways. I mean one that might be a little bit counterintuitive is often times it can fall down before the first call even happens. I know there’s been a lot of research done to say you know buyers’ minds are something like 60% of the way made up before they even take that first sales call. So this really comes down to SDRs, to marketing, how are you qualifying leads? How are you messaging about your product? How are you educating customers as they go out and start to research additional options on their own? So that’s one way I think about it, is all that stuff that happens presale is super critical to getting a high close rate. But then, also, it’s company specific and you really need to dig in with your sales or revenue ops leaders and figure out what parts of the funnel are you losing opportunities? So it’s gonna be different for every company. Some companies might lose a lot of opportunities after the first call. Some might lose opportunities after the second call or once it gets to pricing, but that kind of data can be really powerful for thinking through what changes you need to make.

Here at Rainforest we actually take it one level deeper and so we look at it on an individual AE basis where are opportunities falling out of their funnel so that we can provide specific coaching and feedback to say this is some area that you need to improve upon.

Harry Stebbings: No, I love that kind of post mortem approach, but it does lead very nicely into my next question, which is really all around feedback ’cause we’ve assessed kind of time allocation across pipe and strategies to optimize win rate, but having worked in multiple organizations in teams, what do you believe then is the right mechanism for feedback delivery?

Hannah Willson: Yeah, so I very much believe in continuous feedback. I think the annual performance review everyone knows is sort of a thing of the past where you’re just giving someone feedback once a year. We really do it continuously here at Rainforest and one of the things that we–actually started happening before I even joined Rainforest, but I was so excited to see is this concept of peer feedback. So the team would get together every Friday, fairly light atmosphere and play someone’s call from the week and maybe it was a specific competitor that we were coming up against or maybe it was a specific objection we started hearing and people would get around a room and we would play the call and the replay of the call and everyone would say you could have done this better. I wish I had done this better. You have to be pretty vulnerable to do that but I think that’s where the magic happens because often times your manager doesn’t know how to sell better than some of the AEs on the ground and often times certainly your VP doesn’t. So I think learning from your peers is really, really critical.

Harry Stebbings: I love that element of learning from your peers for that. Are there any inherent challenges or maybe guidelines that need to be set up front and addressed when imposing quite a candid and transparent strategy of feedback delivery?

Hannah Willson: Yeah, I think it’s just important that it’s never punitive. It’s never you did this wrong on a call. Why did you do this? It’s just setting this atmosphere of we all want to get better every day. I would play calls I did and I would literally cringe listening to them, but I think you have to set the tone that everyone has strengths, everyone has areas that they can improve and we’re in this together. We have a team goal that we’re working towards every month, every quarter, every year, and we lift each other up and we help each other get better. So it’s creating this environment of positivity is really important when you’re giving critical feedback.

Harry Stebbings: No, I love that environment of positivity and I couldn’t agree more there, but I do want to move into my favorite element of any interview called the 60 second SaaStr. So I say a short statement and you give me your immediate thoughts. Are you strapped in and ready.

Hannah Willson: I think so.

Harry Stebbings: Okay, Lars Nielson, we mentioned before said SDRs are the most important function of the process. Do you agree?

Hannah Willson: I do. I mean not only from a quantity standpoint. Obviously they’re bringing in most of the new leads for a company if you’re in a primarily outbound environment, but also just setting the tone, as I mentioned before, of setting really high quality, which can definitely impact your win rates long-term.

Harry Stebbings: Sales rep productivity, what’s good in your mind?

Hannah Willson: Yeah, so I think that there’s obviously, I think SaaStr has some data on this and we have about a $1.4 million quota for our AEs, which we feel like is in line with market from a productivity perspective. If you want to look at it a little bit more simplistically, I sometimes look at how many new first sales calls can a rep sustain every day while still being able to keep a high close rate. So that’s gonna be different for every company. Maybe it’s three new sales calls a day, maybe it’s one. It’s a very simplistic way to look at rep productivity and then also, of course, just looking at the conversion rate and if you have those AEs that have lower conversion rate, what can you do to boost that.

Harry Stebbings: In terms of your reading material, tell me what’s the favorite SaaS reading material?

Hannah Willson: Well I’m playing to my audience a bit here but since I got into the world of SaaS, maybe five years ago, I think I’ve consumed most everything that’s come out of SaaStr and it’s been amazingly helpful for me, but also I sort of go back to my roots as a consultant at CEB Gartner and the research coming out of there from a sales perspective is really second to none. They do a rigorous survey, an analysis of thousands of sales organizations. So really strong from a data perspective and I’m always looking at what they come out with as well.

Harry Stebbings: Then final one, and probably one of my favorites, what do you know now that you wish you’d known at the beginning? Now you can choose a beginning, being the beginning of your time with Rainforest, the beginning of your time with Zenefits or even entry into SaaS first.

Hannah Willson: You mentioned this to me before the call and it took me awhile to think about what this could be. I mean there’s just so many learnings every day. I think the two biggest ones, and they sort of span your entire career, one is just going back to what I said earlier about being vulnerable. Whether you’re an AE, whether you’re a leader and just always having that learning mindset. Always putting yourself in uncomfortable situations, always trying to get better every day. I mean it sounds so simple but I think with sales in particular when you have a monthly quota and you start doing something that’s working, it’s hard to get into that space. So that would be my biggest advice both for AEs, as well as sales leaders.

Harry Stebbings: Hannah, it really has been such a pleasure. As I said, I heard so many great things from Russell, Fred, and from Sam. So thank you so much for joining me today.

Hannah Willson: Yeah. Thank you. This was fun.

Harry Stebbings: What an episode that was. Now I want to say a huge thank you to Hannah for giving up her time today for the show. I do also want to say a huge thank you to Fred and Russel at Rainforest QA and Sam at Brex for the fantastic question suggestions today. That really did help me so much, but before we leave you today.

As always, I so appreciate all your support, and I cannot wait to bring you a very special episode next week.


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