Can I Offer You Some Feedback? - Episode #100

Show Notes:

In this episode, Sara interviews Carrie Aguilar, a coach and consultant specializing in tech startup sales strategy. Carrie shares her background in tech sales and her experience in managing and training sales teams. They discuss the challenges of remote work and the importance of trust but verify in managing sales teams. Carrie emphasizes the need for a sales strategy in startups and the importance of understanding the problem the product solves. They also discuss the importance of delivering honest feedback and the impact of having a deliberate sales strategy in a startup environment. Subscribe to the podcast for new episodes weekly!

Episode #100: Consultant Insights: Trust by Verifying

Sara: Welcome to a special episode of, Can I Offer You Some Feedback? My name is Sara, and this is the podcast for those who have a complicated relationship with feedback and are looking to hear from real people across levels and industries with their ideas, perspectives, and best practices on feedback.

Today, I want to share a special episode where I talk with another coach and consultant who specializes in tech startup sales strategy. In this episode, we'll be hearing their insight across industries and what they would like to give their clients feedback on. I want to welcome Carrie to the podcast today. She's the founder and CEO of Innovate Growth Partners. Welcome to the conversation today.

Carrie: Thanks, Sara. How are you?

Sara: Doing good.

Carrie: Great.

Sara: I want to dive into the conversation with a little bit more information on your specific perspective. Can you share a little bit about the primary areas of your practice and how you support the organizations you work with?

Carrie: Yeah, of course. Can I actually start with a little bit of my background?

Sara: 100%.

Carrie: Because I think that would be... Okay. I actually started in tech sales years ago. About 15 years ago, I started pre-IPO at Yelp where I did ad sales for them. And during that time, Yelp hired and onboarded about 35 or 40 new ad sales reps every single month. And so I joined, I think it was like November of 2011. We went public in I guess, March of 2012. And so I was in this space of lots of feedback because in sales you needed to get really good really quickly or you were job.

So, I was in this very heavy feedback phase and very heavy coaching phase. And I lived there for about five years. I moved up through sales and into managing and into training. I ended up actually as a training manager there. And then I accelerated my career through. Became head of training at an ad tech company, and then spent the last five years as head of training, actually, sales training and enablement at DoorDash.

And so during that time, I joined when we were Series C, and then I left in June of 2023. And when I left, my team oversaw about 1,300 different folks where we were in charge of developing both on the skill side, the product side and the tooling side. I think to give you kind of a little bit of background on my primary areas, it would be actually on developing sales strategy for startups, number one, because that's what I did both at Yelp and definitely at DoorDash. Also on helping managers and leaders develop their people and develop their salespeople to be the best possible salespeople they can be. And that's really what I do day in and day out now with Innovate Growth Partners.

Sara: Yeah. I really appreciate you sharing that context. And also for folks that aren't familiar with startup, it's helpful to know kind of the different phases at which you entered and how different that is, right? So, Yelp pre-IPO is not the same as Yelp today.

Carrie: Right. Absolutely.

Sara: Very different kind of style and agility, as you're saying. Not just in sales, but in the rest of the org, you got to move fast and you're getting feedback all the time, whether or not it's actually being delivered, the decisions the customers are making is the feedback that you're receiving 100%. So, excellent.

I'm curious if you could share a little bit, obviously, you've been in this space a while from a couple of different lenses, and COVID, of course, has had a huge impact. What has felt different now that you're kind of looking back at the past four years and thinking about how either strategy or tech approaches or even just startups have changed post-COVID? Or something that you're hearing your clients ask for more of. What does that look like?

Carrie: Yeah. What's interesting is I think there's two pieces. There's the piece that is pretty common which is trust, but verify. So on this sales side, it's very easy when you are physically in a space and you are managing or you're a sales director or even you're a founder and let's say you have a group of five people that are sales folks and they're inside sales folks. And their expectations are to make calls every day and to have conversations with business owners every day. You know, you're physically in the office with them, listening to them on the call.

So, you know that they're doing their jobs. You know that you can look over and if it's an open bullpen space style, which most tech offices are, you can see that they have LinkedIn pulled up, they've got their in mails up, you know, they're doing what they're supposed to be doing. And I guess that's a natural move throughout their day to be able to see that.

With COVID, understandably so you're working from home. So there's a whole lot less. Well, there's now an inability to be able to... and it's not even micromanaging. It's just making sure that your people are headed in the right direction in the casual way that you did before. Now, that way is not possible.

So, what I always talk about with my clients is the need to trust, but verify. And so having accountability metrics in place with their folks. It doesn't need to be a micromanaging type situation. It just needs to be, hey, these are the expectations. The expectations are quarterly, we expect you to close seven big projects. To be able to do seven big projects, we're expecting you to have 20 conversations. Do you see what I'm saying? And you actually work backwards.

Sara: Yeah.

Carrie: And that actually needs to start with top of funnel. It needs to start with output. It needs to start with the amount of emails you send a day. It needs to start with an amount of phone calls that you have per week. But you need to be able to have a way to track that. And then you need to trust that your people are doing it. But you also, at the end of the week, need to verify that. Because if you're not doing that, what you'll find is that people aren't doing that. Or you're trusting that they're doing it. You know, you're assuming that they're doing it and then a month goes by and you're realizing that they're not doing it at all. And then you have to have an awkward conversation that's just like, "Hey, you haven't picked up your phone."

Sara: Right. And I think a lot of organizations kind of pre-COVID the trust was, well, they look busy, so I trust that they're working. And I think before, verify was an issue also. I'm not sure folks were doing a great job of verifying before. It's become more needed. And again, not that I want to be on people, but I should know what folks are working on, and I should know how they're doing, I should know if they need help. And so it just changes the way we do that, and makes it, in some cases, harder to reach out and ask for help. But a good manager who really cares about the development of their folks finds ways to do that, that don't feel overstepping.

Carrie: Well, and I also think that communicating in the beginning that you have expectations that look like, you know, these are your output expectations. And unless you are hitting 200% to your quota or unless you are hitting 200% to your expectations, this is what we expect you to be hitting and being clear on that from the beginning, then there is no awkward conversation that you need to have because, from day one, that's what you're expected to do.

Sara: Right. Absolutely. I'm wondering if, and you've had the benefit of both working inside and now you're outside organizations. Sometimes when a client is expressing what they're looking for, what they're struggling with or what their challenge is, it feels kind of obvious to me. Or I feel like I have a pretty good sense of it. But for them, it's been so gradual and it's been building over time, or maybe they're choosing to ignore some really big elephant in the room. What are some of the ways you work with your clients to help them see what you are seeing?

Carrie: One of the best ways that I do that is, and I'll use this as an example. So right now I'm working with a client on doing some SDR coaching. So I'm working with them on, essentially, not only working with the founder on their ability to level themselves up on what should coaching SDRs look like, but also helping the SDRs with how do their calls sound, what should their calls actually be sounding like and then be able to provide concrete coaching on a weekly basis.

And what's been amazing about that is there were some pieces of information that I was able to think about before the founder came to me with some issues. Immediately I was like, oh, I know that this is going to be an issue. This is going to be an issue. This is going to be an issue. And it was going to be like DM process. It was going to be like not setting great appointments or strong appointments.

And so I started asking people, the SDRs themselves about their show rate. Like do they have people that no show them? In the beginning, they had said, "Oh, no, I've never had that issue." And in my head, I'm like, "Like really?"

Sara: What kind of magic sales are you doing?

Carrie: I've been in sales for a really long time. And these are people that I have listened to their phone calls. But what's interesting is when you do the work with them, when you listen to the calls with them, so what I do is like, let's say Sara, you are the SDR, then I would listen to the call with you and ask, "Okay, what sort of feedback would you give yourself?" And typically they're pretty self-aware. They would say like, well, I didn't ask this question or I didn't ask this question. I'd say, "Great, next week, this is what I'd be looking for." I'd give you three pieces of feedback. I send you a recap email, and then I CC the founder.

And then what I do is I have a conversation with the founder and I say, "Hey, this is what I'm hearing. This is what they're seeing. But I also want you to listen to this so you can start to pick up on it too." And I think that has been really helpful because the questions that I initially were asking him were like, "Hey, did you ever have this issue?" Or "Were you ever having this issue?"

At first, I think they were pretty hesitant to say yes. Now they're pretty obviously like, "Yes, we have had a problem." Okay, great. We need to define this. We need to define what is the decision-maker? How much do we care about setting an appointment with the decision-maker? How many appointments do we want them to set? That sort of thing. So doing the work with them I think is very important.

Sara: Yeah. I'm assuming the SDR is like a sales delivery representative or something.

Carrie: Yeah, development.

Sara: Development. Okay.

Carrie: That's fine. That's fine. We have like a million different acronyms.

Sara: I was close. I love that you asked them, what feedback would you give yourself? Because they know, right? They know probably 80% of what they could do to improve and maybe you're giving refinements on it. But people know. And, and the hard thing about the call is, you know there's like 20 things you have to do and then like when you're doing it, some stuff gets missed, right? No one's perfect. You're not going to get 100% of the stuff, but I love that you start with that question. What feedback would you give yourself? Let's document it. Here are some ways to work on it.

I think that really respects the person that they know their work, they're the professional, let me hear it from them rather than me offering them obvious things that they already know. We might agree on it, but leading with them, it definitely helps support that and helps them feel like they're a part of it as well, which also makes a difference if they're going to give you the time.

Carrie: And I would say the caveat there is I always make sure that I prep myself for the call. So I never go into a call blind and I always listen to the calls beforehand and have notes myself. That way when I ask them, "Hey, what would you do differently?" Or "How are you feeling about this call?" I know what I'm kind of searching for. And I'm not just pulling at straws. I have those threads that I'm looking for that I'm like trying to make up on the fly.

Sara: Right. Well, because I would imagine that only listening to one call doesn't give you context for the person.

Carrie: Right.

Sara: And if you did, let's say like five samples beforehand, you know that in general, this person does this, this, and this. So now you know whether the call you have is representative-ish. It's not going to be perfect. It's not going to be all the calls they do, but it gives you enough to know, oh, this one was unusual or this one, I did see this theme and therefore it's supported. So I really like that.

I'm curious for the clients that you're working with. Obviously, they come to you because they need assistance with sales strategy and how to do that, especially in the tech startup space. I'm wondering if there's a client, whether you want to keep them anonymous or not, is up to you, where you feel like they're really doing it. They're really listening. They're really committed to doing the work. Because it's one thing to bring you in and then not listen, which a lot of folks do. But I'm curious if you have a group that really is showing that dedication and really showing the investment, not just like paying the bills, but actually really believing in what you're sharing with them.

Carrie: Actually, the example that I just used, the founder, like three weeks ago, we were talking and you know how, or at least for me, I have two monitors and so when I'm communicating, I'm communicating on one monitor and then sometimes I'll be doing other things on another monitor. You know, when I was at DoorDash, it was a terrible habit, there was always something better to be doing. They were always... I'm trying to think of our mode of communication, which I can't think of right now.

Sara: Slack or Trello or Asana or whatever.

Carrie: Yeah, they were always slacking. And in this conversation a couple of weeks ago, it looked like they were communicating with someone. And I was like, "Hey, do I need to give you a minute?" And I wasn't trying to be rude nor was I trying to call them out. I was just wanting to make sure that I wasn't talking over like they need to put out fires and I'm not a fire to be put out. So, I'm happy to be quiet.

And then he turned to me and he's like, "Oh no, I'm just making notes on what you're saying." And I was like, "Oh, okay." It was as if he was doing a dictation. It looked like he was writing down every last thing I was saying.

Sara: Wow!

Carrie: But it was just a really nice piece because sometimes you work with people and you're doing a service, you go through the ins and outs of what you do, your standard operating procedures, you go through your exercises, and sometimes it goes in one ear and out the other. And it was just really nice to have someone be like, "Oh no, I'm just writing down every last thing you're saying." I was like, "Oh."

Sara: "I'm creating my own transcript, right?"

Carrie: Yeah. I was like, "Oh, okay." But I would say they do a very good job of implementing. And also, one of the things that they've done a really good job of is actually, so I'm doing coaching for this group of folks, but then he's actually taking on some of the harder cases, which I really appreciate. And he's like, "Listen, I need to learn how to do this and take it on," which is wonderful. Instead of just outsourcing it, which kind of what I was there to do. So, it was wonderful.

Sara: I mean, it does show that they are wanting to see how they can apply the learning. Because at a certain point, you have to leave them. I mean, they could pay you forever, but that's not practical. And so at a certain point, they do need to step up and do the conversations themselves and get feedback on how that's going.

I'm curious, I know you're working with a wide variety of clients, and even if it was before your current practice, sometimes we see that no matter how hard that person is trying, it is just not working. And we sometimes have to tell that person like, "It's not working. It's not going to go forward. We need to pull this project," whatever that difficult or hard feedback is. How do you think about or what's one of the strategies you use to deliver that feedback about how that person's actually doing? How do you prep for that hard conversation?

Carrie: I spent a lot of time thinking about this. I think these are some of my best conversations. And I think they are some of my best conversations because I start them like this. I say, hey, I have thought about this a lot and this conversation can go one of two ways. I cannot tell you how I'm really feeling. I can Keep going forward and keep encouraging you and we can keep trying to figure out the best way to shove this square peg in a round hole. Or I can do what I've decided to do, which is be really honest and say, I'm not really sure that either our relationship or this product process or fill in the blank is really in your best interest or in our best interest. And I've really hemmed and hawed over it. So I'm just being honest with you and I'm going to be quiet now.

And usually, people really appreciate that. I would say sometimes I hold onto that more than I should, meaning, I have that conversation a little later than I should. And that's something that I am trying to get better at in my practice and in my business. But I do do it well when I do it.

Sara: I really like how you open up the space for the conversation and it's hard, but that's why they have us, right?

Carrie: Right.

Sara: They say they want to hear, whether or not we're going to respond well, but how we prep it and how we hedge it and how we support it again, obviously depends on the nature of the relationship you have with the end client. But it doesn't mean it's easy. But at the end of the day, I can keep doing this but this is not helping either of us, whatever it is and I want what's best for you and I think that being candid with you and being upfront with you is the best way to do it. So, let's talk about it and not beat around the bush or ignore it for another blank months because that's not a good use of either of our time. I really like that. It is a straightforward and kind of upfront way of doing it, which I think is very much your style. As you say, people really respond well to that. They want to hear that candor. They want to hear that honesty.

Carrie: I don't think they would have hired me if they didn't.

Sara: Right. And like, I don't want to work with people that don't want to hear it. If you want someone to just tell you how great you are and pat you on the back and say all the nice fluffy things, I'm not your person. I mean, I'll say nice things to you, but that's not why you brought me in.

Carrie: But you're going to earn them.

Sara: Having a sales strategy feels like an obvious thing that's important yet I'm sure that you are sometimes in organizations where it is obvious they don't have it. And I'm wondering if you could share a little bit about what do you wish other people understood about the potential impact and having a real deliberate sales strategy, especially in a startup environment? What difference does it make that people are missing? Why don't they get it?

Carrie: I think this is a conversation I have a lot. Understandably so, I suppose. I talk to a lot of founders who really love their product and they might be very tech-forward and they just are so obsessed with the product or they're obsessed with the problem. So the problem is the issue that they're solving, or the product is like the fancy thing that they decided to build. And what I have found is that sometimes there is a big breakdown in understanding the product versus the ability to get people on board with the product and the ability to sell the product.

And so that would be the piece that I would really want to hit home is everyone, or every startup that I have really spoken with now over the course of last year is really like, how do we fully understand, yes, your product, but really like, what is the problem that you're trying to solve? And how can we paint the picture or how can we understand your client as much as we possibly can so that your product can really solve that issue? And that's really the piece there. That's the sales strategy piece. I think that's a big piece of it.

The other piece of it is I work with a lot of businesses that are trying to either raise money or they have raised money and they're trying to raise more money. And VCs typically want to see some amount of sales strategy or some amount of path forward. And the greatest thing about it is they don't need the right path forward. They just need a path forward.

So, committing to a path forward with some sort of defendable thesis is really the key. So just having something and this is my path forward, whether it's right or not is really not what's important is paramount. So it's paramount to getting funding. It's paramount to getting people's buy in. It's paramount to getting people to really understand, oh, there is a place for this. There is a home for this. There is a need for this in the ecosystem is incredibly important.

Sara: Yeah, absolutely. I hear you 100%. I meet a lot of folks who are so driven by the mission. They're just like, if we build it, they will come. And I'm like, but how will they come and when will they come and where will they go?

Carrie: And who is coming?

Sara: And how much will they pay? Because it's not just, is there a problem, but who's going to do something about it?

Carrie: Yeah. And is the problem worth solving?

Sara: Right. I remember kind of early in my coaching, I wanted to work so much with juniors and seniors in college who needed career counseling and coaching. A great market, a market that needs it. Who's paying for that? A parent is not necessarily going to pay. The school already has a career services doing their best, but just because it's needed doesn't mean there isn't someone to offer that. And then it becomes a privilege and access problem. It's already a privilege and access problem just by the nature of networks, but it's not that there isn't a need. It's just who can pay for the services and who can pay for the quality of that experience. So, very much an important thing for folks to think about a little bit deeper. Well, I'm curious for our last question in our time together, Carrie, can I offer you some feedback?

Carrie: Oh, please! I'm so excited for this! I'm so nervous though.

Sara: I know! I'm here for it! I love that we've had the chance to reconnect. For listeners, Carrie and I go way back to high school. But I think that one of the things that--

Carrie: It's actually to middle school.

Sara: Well, it felt like on the cusp of, in my mind, eighth grade was the year. We kind of reconnected even just this past year and you were talking a little bit about starting your practice and getting things up and running. And I was reminded in our conversation, about the same spirit I felt when we were younger, I perceive, that you have this unbelievable confidence and like, I can do that.

And I talk to so many people, no I'm serious, I talk to so many people who come to me and who are like, I want to do what you do. And I'm like, okay, here's what you need to do. And then like, oh, that sounds hard. And then like, it doesn't actually happen. And you and I chatted a little bit and you were like, "Oh, okay. No problem." Like, I'm going to work on it and here's how it's going to go. And I'm guessing a little bit of that is the startup mindset and you've just done it and figured it out. But it just felt so perfect. I was like, of course, Carrie has been successful in this environment. And of course, she's perfect for this. And like, whether or not it's all like a facade, that's not the point.

Carrie: Totally a facade.

Sara: But for me, I was just like, yeah. I know for me, it took me years to build up my own mental confidence around, I can do this and I can step into this. And I just love seeing your example over the past months of just like running with this. And that's been a different kind of reinvigorating for me every time I see your post and every time I see you know you're writing this and you're presenting at that and you're attending this and I'm just like, yeah! Like, we can do hard things. And so it just feels like exciting. And so I'm glad we reconnected and I've been real grateful to kind of see that just excitement and like zest that you're throwing yourself into this so I wanted to say thank you for that.

Carrie: That brings tears to my eyes. Thank you so much. That's so sweet.

Sara: This is hard work. Well, we're doing is hard work and being alone.

Carrie: I know. It really is. Thank you.

Sara: We're like alone, but not alone.

Carrie: But why didn't you tell me it was so hard? No, I'm just kidding.

Sara: It's the kind of thing you can tell people, but you don't know until you know, and then you're like, it's too late.

Carrie: I feel like that's also like having kids too.

Sara: Yes.

Carrie: I know that's a whole thing.

Sara: Concur. Concur. If someone had told me the sheer amount of meals I'd be cooking, I would have just noped out of it. But here we are and I love my kids.

Carrie: That's so funny. Well, thank you.

Sara: But Carrie, thank you so much. Thank you so much for taking the time to speak with me. And thanks to you for joining us in a special episode of Can I Offer You Some Feedback? You can reach me at podcast@mod.network. We would love to hear from you and your thoughts on feedback and any other perspectives you'd like to hear from next. As always, give us a quick rating on your platform of choice and share this podcast with a friend. And I'm hoping that tomorrow you take a chance and offer some feedback when it's needed most.