The Top 10 Interview Questions for a VP of Marketing!

Jason M. Lemkin’s YouTube talk gives a practical, startup-focused checklist of the top 10 interview questions to vet a VP of Marketing (or first Head/VP hire). He emphasizes listening closely to candidates’ answers to avoid mis-hires, and focuses on concrete, revenue-oriented topics: candidate priorities (top 3 marketing upgrades), whether they had a measurable commit and hit it, collaboration with sales, marketing budget and team sizing tied to ARR goals, tactics for demand gen and win-rate improvement, segment-specific playbooks (including ABM vs high-volume channels), agency selection, brand vs demand balance, and customer marketing to drive NRR/ARR. The talk includes numerous hiring red flags (charisma without delivery, no commit history, oversized team demands, wrong-segment focus, over-investment in brand early).
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Hey everybody. Recently we did one of the most popular tweets and LinkedIn posts that I've ever done which was on the top 10 questions to ask a VP of Marketing in an interview to make sure you don't do a mishre. And we had almost a thousand likes, hundreds of retweets on this relatively succinct post. And I wanted to take some time to dig in here to really give you the this list of the 10 key questions to ask, especially when you go to hire your first VP of marketing to talk about why they matter. And we've spoken so much on Saster over the years on making sure you hire the right VP of sales, when to know you haven't and how to get this critical hire right. And boy, when you hire the wrong VP of sales and if you have, you'll know this. It's like driving a speeding car into a wall. I mean things fall off, tend to fall off the rails pretty quickly. They hire the wrong people, they argue with the wrong people, they miss all their goals, they blame other people. It's a long and as terrible a hire as that can be if you're honest about it and you don't give them too many chances. You'll know in a sales cycle because things don't get better with the VP of sales. The VP of marketing, you'll know too. But people let it go on for longer. Marketing can be a softer art. The goals are often leads, contacts, opportunities, pipeline. They're not always revenue. And a lot of marketers talk the talk and they can often make you feel good. They're marketers. They often are good at marketing themselves. And so we hire the wrong people. We hire the people we hope and believe can do the job, not the people that can actually do the job. And that's what happens again. And I'll work with a great founder and they'll ask me to meet with their VP of marketing candidate and I'll discover they don't really know how to do demand gen or they're not really interested in the type of customers that are most important at the startup or they need an army of people to get anything done. And I explain this to the founder that why it will never work and they don't really want to listen. They sort of fall in love with this candidate that's marketing themselves. So you got to be careful to not do that. A charismatic marketer, frankly, can sometimes be a negative. This is SaaS. We want to put points on the board and too many especially CMO types are even better at marketing themselves than the companies and products they work with. So I almost prefer a very technical marketer that doesn't know how to market themselves but just can show you a funnel and how funnel management works and how they got more revenue into the company. Maybe that's it boils all down to that is hiring that person, the senior marketing technician, not the person that loves to promote themselves on their own podcast and their own social media channels. But let's go through 10 questions. If you ask these 10 questions to your to your candidates for VA marketing, you listen. Not just ask, but listen to the answers and listen to the ones that aren't the greatest answers. There won't be terrible, but they won't be greatest. And rule out the ones that fail this test. You will avoid a mis hire. You will avoid the fact that a majority of you will make a mis hire. So let's go through the 10. The first one, it's so simple. But when I interview marketers, I ask this too. And I ask it Colombo fashion. I ask it with a smile, but I just say, hey Bob, hey Linda, hey Jim, hey Jane. What are the top three things you think we should upgrade in marketing? And this is a great leading question because these candidates are there for vp, they're for head of, they're confident, they've been doing it for a while and they tell you right away the top three things and listen and listen and why that's all they'll ever do. There's so much to do in marketing. There's product marketing, brand marketing, corporate marketing, demand gen field marketing, abm, the website, social media strategies, content marketing, customer marketing. I mean there's so much to do that maybe almost forever you can't do it all. And certainly for a long time you can't do it all. So you have to listen because there's so many facets of marketing. And these candidates will tell you, they'll tell you the top three things they want to do. And I can tell you my experience, they basically never change. And in particular if demand gen isn't in the top three, they never really do it. They never really get you more leads. I was working with a startup with a great new head of marketing who came from a great bigger startup doing hundreds of millions of revenue. Very intelligent candidate, very likable, very charismatic. But that company was so big, the brand was so well established. None of in this top three was generating more opportunity for sales team. He'd done it in his career. But I asked him what the top three was and it wasn't there. And you know, the truth is he never did it. He had done it, but he never did it wasn't his top three. So just ask and listen. And if you don't like what they think the top three things they should do, don't try to change their minds. You can and they'll engage with you, but trust me, they'll never do it. Marketers only want to do spend half of their time on the three things they love to do. And if it's not the first three things they tell you the first thing, first three things they think you should upgrade. You have the wrong candidate, at least for your startup. It's just a mismatch. Okay, point number two, super simple question. You can almost get to the to figure out if you have the right marketer just from these first two questions. So the next one is which I always ask, you know, Jill, Jane, Bob, John, what, what commit did you have in your last role and how much of it did you meet? It's a great two part question. What was your commit and how much of it did you meet? So many marketers you will meet did not have a commit. What is a commit? A commit is a number just like a sales number that a marketer has. It could be for leads, it could be for opportunities, it could be for MQLs, it could be for sales accepted leads, it could even be for pipeline in general or sometimes in bigger, with bigger deals it's often revenue sometimes. And I don't personally love this, but it's become commonplace that in the enterprise marketing owns the same revenue number of sales. In any event, what's their commit? And you will find that 80% of the candidates didn't have a real commit. Maybe their boss did, maybe someone else did, but they did not have a commit. And then ask how much of it did you meet? And I love this question because the truth is a lot of marketers, they don't meet their commit every year. It's hard. A lot of marketers don't get enough budget and they're expected to hit crazy amounts of pipeline generation and they come up short. And I love to hear why that happened. What's the story, you didn't meet it. Every salesperson, it seems like is in president's club. Every salesperson blows out their quota. But it's not true in marketing and I love to learn why. And if the answers aren't fluent, even if they say they had a commit, but they can't tell you how much of it they met, they can't do it. They've never had a commit and you're not ready. You should not be taking that risk on ahead of marketing that has not had to commit in their last job. Maybe they can be on their team or something, but the wrong person. So again, these two questions alone are going to get you there. What are the top three things you think we should upgrade? And two, what commit did you hold in your last role and how much of it did you meet? But let me give you eight more to just keep that conversation going and make sure the third one and you will learn so much for this. How have you worked with the sales team in the past? And if you have a sales driven SaaS company, you may think this is natural. Of course marketing and sales work together. You know my companies, they always sat together. You know, back when we, back when we weren't all distributed, they would literally sit in the same place because it was hand in hand. Marketing's job was always at the end of the day to make sales more successful. But I would say the majority of marketers have not had that experience. The majority of marketers have not not worked hand in hand with sales and certainly not with a head of sales or a VP of sales. And so ask how have you worked with the sales team in the past? Get the anecdotes out. And sometimes you can take some risk here. But when you hear great stories, when you hear how he or she worked with their VP of sales and how there was good times and tougher times and how they worked together and they were in the trenches together and what they are and you can ask what they argued about. When you hear that dynamic, that's the magic that you want in a revenue generating marketer. Okay, point four. I love this one. What should our marketing budget be? You would be surprised how few candidates can answer this question now. In all fairness to them, most CEOs don't give marketers enough information. I'm shocked I asked this question to so many candidates. What do you think the marketing budget should be? And they often don't even know what the ARR, if the company is say or what it'll be in a year. A marketer can only answer this question if you give them information about the company, what the ARR is today and you have to tell them what it's going to be in a year. So when I help CEOs I say look, this company is at 5 million and our goal next year, 12 months from now is 12 million. So we need to add plus 7 million of ARR. What should we, what should we do? And if the company knows enough, if the candidate knows enough about your acv, your target Persona, what's working, what isn't, they'll have a pretty good sense. Now their answer, you may not like it. They may say look, if we need to add 7 million of ACV, given how lead poor the company is and all this, I need 5 million. And that may scare you. Maybe they do need 5 million to generate 7 million. That's not very efficient from a marketing to revenue perspective, but they'll have a sense based on their experience and dig in here, understand what it's going to be and I love the answers here. And question five is related. Once they know your ARR today and their error in a year, ask how big a team we need and the best marketers will have that experience. They'll know to go from 5 to 12, say to add 7 million in bookings, to do it the way I want to do it, to do it with demand gen content marketing business, I need a team of five plus, that's six plus an ops person. I need seven. And you may choke when you hear that if you're bootstrapped or lightly funded. But this is a great question too, because the marketing budget question before shows that they know how to deploy money and think about budgets properly. The bigot team does that too. But it also shows just how much work are they willing to do themselves. There's so much to do in marketing and one of the biggest changes over the last five years is how many seasoned marketers just want bigger teams. They're just tired. They're tired of doing the HubSpot and the marketo themselves and managing 12 agencies themselves and doing field events themselves. Maybe not literally themselves, but maybe with one or two people helping. Now they want an army and I don't really blame them. There's so much to do in marketing. I would want an army too. But sometimes the army they need is too big an army for your budget. So I've seen this again and again where a CEO, especially sort of in that 5 to 10 million error range, sometimes later falls in love with a candidate. They come from a great company, they're charismatic, they're good at marketing themselves and they need like 20 or 30 people to get anything off the ground. And maybe they had that at their last company and it's appropriate. But rarely will you have the capital at that stage to hire that big team VP of marketing. So how big a team do we need. And just listen, listen to the answer. Okay, next. Five, six. I love this one too. What have you done to increase win rates? This is another one to see how closely marketing works with sales. A lot of marketers can't answer this question, but if marketing sees their job as helping a sales team, as work with sales team, they will have done a ton of things to increase win rates because it's not enough to stick a lead in the funnel. If you don't, it won't go to the bottom as effectively. If marketing doesn't help push it down and increase your win rates, what can they do? They can increase product marketing. They could make the website better. They could work on anti fud, anti fear, uncertainty and doubt. They could help, you know, arm the sales team to react to competitive answers during the sales process. There's so many things marketing can do. They can do a weekly webinar where they talk about the competition, they bring customers on, whatever it is. What did you do to increase win rates? Because great marketers, nothing frustrates a great market more than generating a whole bunch of pipeline or opportunity or leads or what it is. And sales doesn't close enough of it. They can blame sales, but the truth is for marketing to succeed they have to increase or at least keep win rates consistent. And so they're always thinking, the great marketers are always thinking about how can they help arm sales, train sales, support sales so that when rates go up and maybe didn't go great at their last job, but it's great if they've thought about it and they can tell you what they've done, then you know you have a marketer that is focused on supporting sales.7 and trust me on this one, this is one where so many folks make a mistake and they make a mis hire. Question 7 is what should we do to market to each of our top three segments? Now if you only have one type of customer, only very small business or only enterprise, forget about this question. But I will tell you, I've ruled out so many helping CEOs rule candidates for companies that have multi segments of customers, say small, medium and large or mid market and enterprise. And I will talk to a VP of marketing and maybe they've done a lot in their career but at this point they want to run a certain playbook. I was just working with a startup that has gone very enterprise. It's crossed 10 million and they have incredible logos and their goal is 200k to $1 million deals now, now they have 50k customers, 20k customers but that sort of 2 to 300k to a million is what they want to do. And I and I asked this marketing candidate who I love, what they thought, how they thought they should approach these markets and this candidate just wanted to run the mid market. They did not want to do the field marketing playbook they wanted to do sort of this sort of social media content marketing generate high run rate lead playbook that was just not going to work here. Here we needed ABM here we needed to identify the top stakeholders in the big accounts and have marketing help sales find those 500k plus deals. That's ABM. That's not spreading far and wide across adwords and social channels and the skin. I just didn't want to do it. So you've got to ask what should we do to market to each of our segments and listen and listen how they force rank your customer segments and again they may change their mind during discussion here I think it's more okay if with more data they change their mind but make sure their playbook is the right one for your ACV if you're multi segment because what will happen is there's so much to do that marketers will only focus on one segment they like. There's another great startup I worked with, I work with that is doing eight figures of revenue and they have an almost equal amount of split between a B2B business and a B2D developer eight business and they had a great head of marketing who hadn't but had no experience marketing or selling to developers and put all of her time into the B2B and a lot of the B2B stuff was very exciting but all the budget went to it and so that was a huge miss great candidate but mismatch for the customer segment where the B2D was becoming not just 50% but even more of the revenue but the candidate it wasn't their passion, it wasn't one of the things they knew how to market. And so you got to ask this question how do we market to our top three segments and just make sure it's a fit for where your business is going. Hey, point eight seems like a subtle question but boy you'll learn a lot. Question 8 what agencies would you bring in to help us and why does this matter? Well look today in the great resignation and when so many marketers often have a 12 month tenure, agencies are a good thing. A social media agency, an events agency, content agency, a PR agency, whatever the right agencies help a marketer scale. You can't Always hire a full time team to do this. And you get specialists sometimes. I mean Hexastra ourselves, we work with a couple amazing content agencies. Incredible. One cred PR that helps us with our speakers, EEG for event production, et cetera, et cetera. So agencies done right are a good thing. They give you leverage and it's often cost effective. But the mediocre marketers bring in tons of mediocre agencies and they often bring in their pet agencies. They bring in some the wrong PR firm that doesn't, doesn't even know anybody at TechCrunch and some crazy social firm that just wants to burn a lot of money on Instagram when it's not close to your target base. So listen, ask what they do and ask who their top agencies are. And if Linda, Bob and James at these agencies are great, if you have the energy, even talk to one or two of them, maybe you'll use them even if you don't hire this candidate. But see whether it's a lazy approach or a thoughtful approach, but the lazy approach of spending 50, $100,000 a month on a bunch of agencies to help the VP of marketing do less work, that's a flag. That's a flag of a lazy marketer. Okay, penultimate question number nine. How do we focus on bringing up. I'm sorry, I'm building up brand and product awareness and this is a trick question because brand matters. And we always knew brand mattered in SaaS, but boy, we learned this with a vengeance the last few years. Every SaaS company at 100 million AR is becoming a billion dollar. AR companies and the ones at a billion are accelerating. The Zendesk, the Hubspots, Octa, everyone's growing faster past a billion. And one reason is the products of course are getting better. But brand matters so much in SaaS. Brand is emote and brand is critical. And you will have what we've called on Saster many times over the years, a mini brand pretty early. A mini brand is not that you're Zendesk or HubSpot, but let's imagine you're not just Zendesk, but you're someone like Gorgias that does a help center just for E commerce. Now Gorgias is a fraction of the size of Zendesk. It's a 50th of the size. But with 7,000 customers on Shopify in the Shopify ecosystem, boy it has a brand, right. You may not have heard of it listening to this, but in a niche, in a segment in help desk for e commerce, 7,000 people love gorgeous. So that's a brand. Even at 1,000 customers, they had a brand. And generally what I found is somewhere around 2 to 3 million in ARR, you have enough customers that love you. If they do love you, they start telling their friends and people in your top niche, your top little segment of your business, people start hearing about you. Not everybody, not everybody has heard about these alternatives to the big guys. But in this segment you have a mini brand. And so you got to invest in it. You got to invest in it, you got to promote it, you got to do events, you got to get your customers on stage, digitally or in the real world. You have to be out there, you have to promote that brand everywhere and invest in it very thoughtfully. So brand matters. But too much of that playbook too early is the land of the big big company cmo. So I like to hear a very thoughtful answer. I like to hear an answer where at the end of the day, maybe 20% of their time is focused around brand. I like to hear how they're going to upgrade the website, how they're going to upgrade the call to action journey, how they're going to upgrade the position of you in the market. I do like that. None of it. They don't really, they can't really do this. And maybe that's okay if they're pure demand gen, but too much of it is a flag. Too much of the flag is they should be working at Salesforce or Adobe or Microsoft or heck, maybe a Twilio or Zendesk on brand entirely, but you're just too early for that. So too much, a little bit, a little bit of brand is good, but too much time on brand, brand, brand is too much. And the last one, 10 is. I just love this. It's a passion of mine and it shows how thoughtful the VP of marketing candidate is. Which is how much customer marketing should we be doing and what is customer marketing? Customer marketing is something we don't think most of us don't think about. Customer marketing is the marketing you do after you close the deal. And think about this in SaaS with many of our customers will last a decade. And not only that, with NRS of 120, 130, 140%, these customers can get huge. A 10k customer today over 10 years could be worth a million dollars, easily a million dollars. So you do all this marketing to get that, that first 10K ACV in the door, but what about the next 10 years growing? How much of your marketing budget should be spent there and with every SaaS company it's not enough. Even the top public companies, CEOs and CMOs, they know we're not doing enough marketing to our base and we're doing too much to help sales. Sales is the squeaky wheel. As you know. I love sales but it is a squeaky wheel. It gets most marketing attention and that's okay. So it's a tough trade off. It's like an engineering how much time in the early days until you have bigger teams, how much time should we put in technical debt? How much time should we put into to tech ops and DevOps versus new features? In engineering it's tough. You want to do all three and in marketing you should want to do as almost as much marketing post sales as pre sales. And we don't get enough budget, we don't build a big enough teams. But I know all the best marketers I talk to are thinking about this, are thinking about how I what marketing I can do to drive up that NRR and thus drive up the ARR target. And when I have a great discussion here, I know I'm hiring someone that is thinking about the future of marketing and not the past. So, so 10 questions. You can almost get there in the first two. The first five is enough. But the key is to listen, listen, listen. Because these questions will help you find figure out if someone can't do the job but they're not really designed for that. Hopefully you have the skills to do that. Although this will do that as well. The questions are designed to make sure it's not a mis hire a misfit. And so you have to listen. You have to listen if they don't really want to market to your segment, you have to listen if they've never really held a commit, you have to listen if they want to spend all their time on brand or promoting themselves. And if you just listen to the answers, you don't even have to have a response to the response. If you just listen calmly and think on it, you will see if you have the right candidate for your company or not.










