The Breakthrough Hiring Show: Recruiting and Talent Acquisition Conversations
Welcome to The Breakthrough Hiring Show! We are on a mission to help leaders make hiring a competitive advantage.
Join our host, James Mackey, and guests as they discuss various topics, with episodes ranging from high-level thought leadership to the tactical implementation of process and technology.
You will learn how to:
- Shift your team’s culture to a talent-first organization.
- Develop a step-by-step guide to hiring and empowering top talent.
- Leverage data, process, and technology to achieve hiring success.
Thank you to our sponsor, SecureVision, for making this show possible!
The Breakthrough Hiring Show: Recruiting and Talent Acquisition Conversations
EP 129: Startup hiring roadmap. Charting success from day one with Kaitlyn Knopp, Founder & CEO of Pequity.
Ever wondered how hiring strategies vary for different stages of a company? Get ready to decode the ins and outs of hiring in startups and scale-ups with host James Mackey and guest Kaitlyn Knopp, Founder & CEO of Pequity.
Learn about the importance of hiring slowly, evaluating candidates, minimizing risk in hiring decisions, aligning on compensation, and fostering open and honest conversations in the hiring process.
0:36 Kaitlyn Knopp's background
1:21 Hiring strategies and lessons learned
10:29 Evaluating talent and interviewing for a startup
15:44 Leadership qualities and hiring process
Thank you to our sponsor, SecureVision, for making this show possible!
Our host James Mackey
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Hello, welcome to the Breakthrough High-Reach Show. I'm your host, James Mackey. Thank you for joining us today. Today, we were joined by Caitlin Canot. Caitlin, thanks for joining me.
Speaker 2:Thanks so much, James. I'm excited to be here.
Speaker 1:Yes, very excited to host you today. Let's start with your background. Could you tell us a little bit about yourself?
Speaker 2:Yes, I have been a compensation practitioner and leader for the past better part of a decade. I've worked at really cool companies from Google Cruise Automation to Instacart and House, done a bunch of consulting in between, when those experiences led me to build my current company, pequity, or a compensation planning software the best, most flexible and secure planning software in the market all based on the pains that I experienced at these various institutions, realizing there was no software to handle the complex needs around comp cycles or equity refresh or promo cycles, so decided to take a step back, build an amazing team and launch the software that we have today.
Speaker 1:I love it. And so the first topic, as everyone might be able to guess, we're going to talk about hiring, so I wanted to talk to you a little bit about your experience. I mean, you've worked at a lot of really cool companies Google and Instacart and now with your own company. I would love to start there, and when you're thinking about building an incredible team of folks, what are some of the most important lessons learned when it comes to recruiting and hiring for your team?
Speaker 2:Oh man, there are so many good lessons out there. I think the first thing is that it's going to be really stage dependent. The people that you're looking for will vary based on the size of your organization and their experience, and it's also going to be department dependent. For salespeople, for example, I've learned that it's best to find someone who has sold in your space, so has a similar buyer, has sold similar contract sizes, so they know how to do those kinds of deals and hopefully they also have experience at your revenue stage. They know the amount of resources that it takes to get through these and that to me is a really good signal of someone who'll be a good fit for your company if they're in sales. But as you get larger, that might not be true because you might have people who fit those three categories who can train someone else to grow up and build in those arenas. So I think that it will definitely be dependent.
Speaker 2:But if I were to give some very broad advice, I would point to the higher slow fire fast and in startup language, hiring slow might mean taking a week, which is still very fast to a large organization. But to draw lines in the sand that force you to evaluate people and this goes a little bit to performance. But I see a lot of places, both small and large, where they say, oh, we hire slow, fire, fast. But it's not really true. It's quite chaotic and it's usually because they haven't agreed on a 30, 60, 90 day ramp for all roles and they're not evaluating people against that or they don't take those ramps seriously. There are a lot of fluffy language in them. There's no metrics that they're driving to. I think that a lot of success at hiring is consistency and it's also being clear in your expectations, because without those two factors you will be very confused about your talent.
Speaker 1:Yeah, I think, just to dial in on the stage relevancy, particularly for scale-up and startup companies, I do feel like it's really important to get somebody that has that type of scale-up experience and doesn't necessarily come from a large enterprise. And just to dial in on sales talent specifically, I remember a few years ago I went on it's called the CircumSales podcast and I was run by a couple of sales guys, one of which is a 6x VP of sales on the board and advises several early-stage companies, and we were having this conversation about how do you know if somebody from enterprise can make the transition into a startup or a scale-up as a salesperson. And I was like, quite honestly, I said that's not really a question I spend time thinking too much about because I just don't recommend it. Yeah, and they were like surely some people can do it. And I'm like, yeah, I'm sure they could.
Speaker 1:There's people out there that can do it. I'm not saying they can't. However, I wouldn't recommend it. Yeah, and so they're like what do you mean? What do you mean Like, why would you potentially remove good people from your pipeline? I was like, well, statistically it's likely not going to work out. And when you're at a startup or scale-up phase, it doesn't really make sense to take that type of risk.
Speaker 1:Yeah, it's better to find somebody who's actually been in that environment before done the job. So again, my company. In the past decade we've helped over 200 companies hire to embed a recruiting and a PEO, and this is just something I've learned.
Speaker 1:It just doesn't make sense to take the risk on candidates that come from an enterprise environment, particularly for sales and try to plug them into a scale-up, because ultimately they're not going to necessarily know how to run more of the sales cycle or for the role to pivot or adapt or adjust as much as it's needed in a scale-up, and also there's just a certain pace that's kind of some scale-ups move at and, quite honestly, if somebody hasn't been in it then we don't know how they're going to react to that type of stress or pressure or just accountability, invisibility and transparency that people have into their work and their metrics and these types of things. And so I'm not saying that people can't do it. I'm just saying that when it comes to hiring, we should think about minimizing risk, particularly in a smaller teams. And why are we taking a bigger risk when we need to? It just doesn't make sense. I don't know if they necessarily agreed with my answer, but I'm like, okay, I think I'm pretty sure I'm right, just based on everything I've seen over the years.
Speaker 2:I absolutely agree, and I think it is its resources. Of those individuals. They, probably at a larger enterprise, had a playbook and it was already a little bit predefined before they got in there and they had all these different softwares. They had Salesforce, they had Zoom Info or whatever. I'm listing a bunch of these just the way I know. Fast products, yeah, and they probably had a team of SDRs and especially early, early stage, like you are looking for a lot of people.
Speaker 2:Most of your early people are going to wear so many hats. Like your salesperson is going to be the SDR, the account exec. They're also going to be the sales solutions engineer. They're stretching themselves across and it's okay, because it's not like you're balancing that many accounts. You're, at the early stage, just so happy to close one. So you're like that is just all we're shooting for. Especially if you're enterprise sales like myself.
Speaker 2:If you are a self-service PLG product like growth motion kind of startup, this conversation wouldn't apply to you. You probably should not hire a salesperson. That's actually another issue I do find in startups where they say that they're PLG and then they hire a salesperson. I think that's missing the point. I think that there's a lot of people who try to follow formulas which I'm sure you've seen. They're like oh, I'm a new company, I have to have a marketing person and a salesperson, I need a CTO and I needed this and I needed that, and there's some truth to it. But what they really need to do is evaluate their needs and talk about where their budget. If you didn't have a person, would there be a tool that you would put in there? So I think that completely resonates with me that these people who come in from later stage companies will struggle. It's not that they can't do it, they're very smart people but they come from a different set of experiences. We've seen that in sales. I've even seen it in engineering talent.
Speaker 2:You have to be careful. They're people who they thrive on a smaller team. There's these engineer personalities who are brilliant at the early days. They do everything and they understand where to cut corners. Because when you are just fighting to survive, especially with a product, you are trying to build the most basic thing as quickly as possible that is as secure as possible. That you're going to have all this tech debt on you Like I'm just going to figure it out later because nothing matters more than just getting that next contract. And then there's this evolution flip where you now have to oh, shoot that, tech debt matters, I need to pay that down. We can't cut corners. We really need this to be a responsibly built and stable product and that change happens pretty quickly, overnight.
Speaker 2:You won't notice that and there's some engineers who don't respond to that, like they don't like going through code reviews. They don't want to be put on this like PR system with a larger team. They really love being like the rogue builder. That's just the wonderkin coder and they can figure it all out on their own. And it's sad, like it really like we've gone through that. We've helped companies through it. It sucks because you have to have these tough conversations and then often the. Either that person will change or they don't, and you have to go back out to the market and rehire and it. You feel so bad because it's the early person. But that's the reality of the scale up If you don't get the, even if they were the right fit for the first six months, they may not be the right fit for the next five years.
Speaker 1:Yeah, it is a really hard part of the job and some people are able to to grow and make the adjustment with the company, and sometimes the folks, for whatever reason, might not be at a stage in their life or they're able to, and that's that's how it is. Hopefully we get plenty of folks that can stay, but it just it really does depend, and so I've been. I've seen like both situations for sure, and that is part of the trickier parts of being a startup executive and particularly as a founder and CEO, because then you start to see some of that on the executive team too. So it's, it can be quite difficult at times.
Speaker 2:You're. I will say that I hope this doesn't offend any salespeople out there, but sales especially, is one of the roles that they Warn you and a lot of sales leaders have talked to her highly aware it's a high, terminal role. There's just a point where you have to pass off to another leader and you'll know it very clearly and they will know it very clearly, like you'll start to see the signals extremely early, and so there's a lot of times that you just have to be comfortable with that being a high turnover and that sucks. Like you get so invested in these people, like I love my team. It's never easy. It's there's never been an easy conversation when someone's left, and that's part of what you take on as being a builder of this team and that's why we have partners like you, of course, to come help us hire these people and set the right expectations. But it's just the name of the game.
Speaker 1:Yeah, yeah for sure, and I also wanted to talk to you a little bit more so about when you're actually interviewing folks, right? What are some of the things that you're looking for? Are there any kind of tips you have when it comes to evaluating talent that have helped you improve your batting average, if you will, and bringing on great people and I could share some stories here too but I'm curious to get your thoughts on what kind of light bulb moments or shifts that you've made in terms of interview process and evaluation of talent to make sure you're getting the best folks on your team.
Speaker 2:Absolutely. I mean, obviously we're a compensation software company and having been a comp manager, I'll tell you, get aligned on that early, especially the more expensive, the talent like they're going to take longer to vet, they're going to take longer to recruit. Don't wait till you've gone like six weeks with that person and now you're like, hey, by the way, that's not going to end well for anyone. So with the pay transparency laws, you can put their range out there. I always tell people the law just says that we have to place a reasonable range that we expect to pay at the time of hire. It does not mean that's absolutely where we'll land. I care a lot. My team sees a lot of comp data all the time, so I'm like we do have to be fair. We will be consistent. It is a range. Let's have that discussion early. It's like a sale, right, like we're not going to commit to a price, but we're going to say, hey, like this is what we come in with and I really like to make it clear that there is a value, right, like we were a startup. There is certain benefits that I can't offer like a large company, but there's benefits that you get at a small company that you won't get a large company. So I think that's a good thing. Being able to offset and lean into those is important. And I do think there's one thing that I love doing, and I don't know if it's just, I have a feeling it's a combination of the conversation itself and the authenticity that you have to bring to it. But I encourage people to have break up conversations or exit conversations in the interview process and the way that those go down, and I do this in my personal life. I did it with my husband when we moved into India the first time. When we got married, I did it with my leadership team. These people are joining a risky situation and it is your baby as a leader. This is your place. Right.
Speaker 2:I go in and I say, hey, I really enjoy this, like you. Obviously, we're at this stage. I want to talk about if things go wrong and I'm a paranoid personality, so I want to disarm the nukes before we get to that stage, because if we go into this, there's going to be tense moments. There's going to be seconds where we make decisions with 80% of the information we wish that we had, and it means that there's a definite margin where feelings can get hurt and where mistakes can happen. And I need to know what your non-negotiables are right. I need to know what will cause you to say you know what, screw it, pectity was not worth it, I don't want to be here anymore. Caitlin made me so angry she went back on her word. That's what I want to know.
Speaker 2:And at first, like when you put it out there, people can be a little nervous.
Speaker 2:Where they'll give you some, expectations are misaligned or blah, blah, blah, and that's where you have to bring your authentic self.
Speaker 2:And so if I'm talking with a sales leader, I can say if, month after month, you're not giving me consistent metrics, right. And if I see that you're listing deals that are not closing, that is going to erode my trust. And if you are not open to criticism on that, if I can't talk to you about the deals and you can't explicitly point to what's going wrong, that will be a deal breaker for me, right, that is a moment where I'm going to struggle with you as a leader, and then you pass the buck back to them and they'll usually come back much more authentically. But I feel like those conversations are just essential, and it's going to give you such a good insight to what they care about, because they're going to tell you the behavior they expect from you and you'll know if that aligns to your culture or not. Right, like you have to read the signals for what they are and, of course, like, by setting that expectation, if they do join your company, you have a baseline to operate from, which I think is important.
Speaker 1:So I actually, so I completely, I agree with this a lot. I think one thing that I like to slow down a lot is the challenges at the company, the hardest parts of the job, and I can be very honest about okay, yeah, there's challenges that arise, like it could very easily. There could be a lot of factors right, it could be something to do with the performance, but obviously it could be something that's market driven or whatever else. But I do think that a fair amount of time should be spent on nothing's going to go exactly as planned and how are things going to like? How adaptable is somebody, how open to feedback are they? It's something that I really and I think, and that's why I feel like looking for somebody that has a lot of self awareness and just awareness of their surroundings, and I think, to me, somebody who's self aware is typically somebody that is open to feedback, because you really can't be self aware without knowing that you're not perfect.
Speaker 1:If I feel like people are more so aware, are gonna more so understand their weaknesses and more so be open to receiving feedback and getting better, and I think that that's like really important as well, and also like when they're sharing what's important to them, it's showing that they're like transparent. Okay, just the simple act of them sharing that feedback with you. Yeah, these are things that have happened and this is like the type of leaders I like to work with. Here's things that like I feel like we could have had a better dialogue around, or there wasn't enough understanding around this, or, yes, I was struggling with this and then I brought to them a solution which they weren't able to implement, and that's like all of those things. But like again, showing awareness, and that's actually like my favorite question to ask people is if you were promoted to CEO of your current employer tomorrow, what would you double down on, what would you change and what would you discontinue? Oh, nice, and all aspects to individual contributors as well, and I love that question so much because I can basically get I can get value that I would get from asking like 10 other questions just out of that, because I'm gonna learn like, how aware are they in the environment? Are they aware of what the high leverage things are that their team can do.
Speaker 1:Do they seem to have a good pulse on what activities lead to achieving the company's goals, I get to hear. Are they gonna be asked? Who are they gonna go to? Who are they gonna learn from? How are they gonna collaborate? What blind spots do they have? Do they know where they're not? Are they self-aware enough to know what maybe they're not good at? Who should they turn to the result? Or do they see things as a lone wolf? Are they judgmental, closed-minded? Are they too, almost like dogmatic in their approach, where they're so confident they're right, or the type of person that understands? Like, okay, in order to prove myself right, let me try to prove myself wrong. Like I can just get so much value from that, and you're curiosity and just all of those things, and so I guess for me it really is about like awareness, how they go about solving problems, confidence, but humility at the same time, like somewhere in there in the middle and oh, absolutely, and I think, yeah, those are more supportive than me.
Speaker 2:It's funny when you bring it up too, and I think this is like a luxury role that I have as like CEO when it comes to hiring, like I am fortunate that I have some amazing leaders right Like I have. Really, I am very proud of the leadership team that we've built here at Packwiti and I have to get out of their way right Like they know what they want on the team. My role is to come in and be like a cultural flag and to be like the glue flag, like I'm across a lot of things. So, not that I'm I do have ultimate veto if I was like, hey, this person is not gonna work, we're not doing it. But I do need to trust my leaders. So a lot of what I also like to do is I'll tell them, like I'm not hopping on this call because I'm going to technically interview a software engineer. Like I'm not doing that, I am gonna hop on and I'm gonna give them this breakup conversation, and I also try to preserve half of my time with people to ask me questions, and I think that this is actually a really strong play for small startups, cause you like there's a lot of small startups that forget that people don't know about them, they can't. There is no article or data on like these people and so they're coming in. They're scared, so you need to like, let them ask questions, and it is so telling what people will ask you about.
Speaker 2:There's some people who I know are just like, so excited when they're like what's the valuation? When are you gonna fundraise? Like, how quickly are we growing? Like, how many companies are customers today? And I'll get people who are like hey, like, how much vacation do we have? And not that this would just preclude them from the role, but they'll also be like and okay, like, how many hours do people work? And will I be called on weekends? And we do try to have a good work-life balance. But that is an opportunity where you can hear okay, this person is scared of the workload and you do have to talk about being a startup, and not that you don't wanna hire that person, but you need to be honest with them.
Speaker 2:It's not a time to be like oh yeah, no, I will never call you on a Saturday, or we all work nine to five and are off exactly at 5 pm.
Speaker 2:It's your opportunity to be like hey, yeah, actually like if something goes down and you're an engineer, I might call you on a Saturday and I try very hard to give you other times off. This is our vacation policy, but I think giving space for them to breathe will tell you a lot about their personality and it'll also help you manage them once they get in. There's people on my team who have brought up those questions who I love working with. I just know that they have strong boundaries around personal time and I'm like that's great, I'm not gonna randomly text you. I avoid sending them after-hour messages unless there's something urgent, and my commitment to them was I will not message you unless it's urgent and they're okay with that, because I heard their question, I told them my expectations and we're aligned, and alignment is the magic word that we're all seeking after. We know the person's a fit for the role.
Speaker 1:Yeah, I think I do. Also. I make a big part of my final decision fight around interviews based around the quality of the questions somebody asks Like to me as we get on a final round interview. You got the CEO on the interview and you're asking me questions about days off. You could have asked that at any other point throughout the interview process. You could follow up with our internal team to ask those. If you got me on the phone, ask me about the challenges of the company, about the strategic direction, about how we're gonna get there, about how your role impacts it, about. I wanna see curiosity and passion about what we're building and doing. Yeah, yeah, get on and ask me basic questions like just what are you doing? You got 30 minutes with me. Yeah, anything that you want to and you're gonna talk to me about this stuff that you could talk to.
Speaker 2:HR To HR. That's what I'm heading for.
Speaker 1:For a follow up email, like to me. That just lacks, like it shows a lack of awareness and it's usually it's a red flag, right, like those types of folks typically aren't gonna be like the builders, in my opinion. Like I'm not saying that, not, maybe sometimes they are, but it heavily influences my decision and also a career decision is one of the biggest decisions you're ever gonna make in your life. Very important If you're not evaluating them and you're just going with the flow, just take whatever is handed to you. I also don't feel like that vibe goes well in startup culture.
Speaker 2:No, you have to be intentional. I don't know if I have a good metaphor, but I do feel like it's skiing through like untreated stuff. You're just like you have to be paying attention, like you can't run into a tree and we're all trying to shoot down this together. There's a team mentality, but you with your career, especially in startup land, need to be intentional because you will hit trees Like you'll accept that one role. It's gonna be the blip on your resume that you wish you didn't have. It's gonna be like a whatever, and I do think that most I operate from the assumption that most people are trying to do the best they can. They're inherently good. So I don't think that people do it and they're not trying to be bad, but I do think people both people with good intentions can have a bad outcome and that's what you're trying to avoid, cause those are so painful and it's gonna happen regardless, like you will.
Speaker 2:We've had it where we've been so certain about a hire, like they were a five out of five, we're so excited about them, and they got in, and it was like, oh shoot, some element that we didn't expect. Like the market shifted, you'll actually find especially early stage companies. We're now past a lot of this. So there's early days where we were changing our branding and our marketing pitch, cause you're just trying to find what works right. You're desperate to find something that fits, and not everyone can adapt and respond that quickly. And I get it. It's chaotic. They're like wait, what the hell? Like? Last week we were selling this and now we're selling this, and I liked the old pitch and I liked the old look Like why are we? And so, as a leader, you have to cultivate and bring them along, but some people just will not. Some people won't get over it. And that's for an employee. I think that it's important for you to know what you're signing up for and what you're coming into, and if you aren't down for that kind of activity, proceed with caution.
Speaker 1:To start up, oh, for sure, For sure. I couldn't agree more. And look, caitlin, this has been a lot of fun. We're coming up right on time here, so I just wanted to say thank you so much for coming on today and sharing your experience with everyone. This has been a lot of fun.
Speaker 2:Thank you so much, James. I love talking about this and if anyone has any compensation needs, don't feel afraid to reach out to my team. I will always geek out on anything comp or hiring related.
Speaker 1:Yes, please do that everyone. We're going to drop Caitlin's LinkedIn profile into the description of the episode and also keep a lookout. We have some really cool releases coming up. Dan Chait, the co-founder and CEO of Greenhouse, is coming on for second episode. This is going to be released. We got Christian Sutherland-Wong coming on the show We've already recorded. He's the CEO of Glassdoor and he helped actually build out LinkedIn's product from the ground up. And we have Amit Yoran, who is the CEO of a company called Tenable, which is a publicly traded cybersecurity company. So we have a lot of really cool guests coming on the show. So make sure to continue to tune in and we will talk to you soon. Take care, cool.
