Deep Dive with Sarah E. Brown

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This is a podcast episode titled, Deep Dive with Sarah E. Brown. The summary for this episode is: <p>Today’s episode is a deep dive with tech marketing expert Sarah Brown. Sarah is a startup mentor, ecosystem builder, and the author of Lead Upwards.</p><p>She and Matt discuss creative career paths—Sarah considered “The Non-Linear Path” as an alternate title for her book—and the unique opportunities startups present. They also share their thoughts on the contrast between startups and large companies, from office politics to overall function. </p><p>Tune in to hear about mentorship, team hierarchy, and Sarah’s take on quitting as an executive. </p>
Non-linear career paths
03:37 MIN
People understand career paths differently today
01:17 MIN
Transitioning from corporate life to startup life
04:10 MIN
Its important to get your hands dirty in startup life
02:02 MIN
Always practice empathy
00:36 MIN
Focus on people's strengths
00:52 MIN
Knowing when to leave vs when to step up into a new role
03:31 MIN
Sponsorship, mentorship, and coaching
04:45 MIN
The "First Team" concept
03:21 MIN
Quitting and leaving well
03:31 MIN

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences, and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder, and CEO of Bolster, and I am here today going in deep with Sarah Brown. Sarah is a B2B tech marketing leader. She is the author of the outstanding book Lead Upwards. She is a startup mentor, she's an ecosystem builder, and she's focused on scaling SaaS companies through customer- centric marketing. But I have appreciated her wisdom on many, many things that go way beyond that. So, Sarah, great to have you here.

Sarah E. Brown: Thank you so much, Matt. I'm really excited to be here.

Matt Blumberg: One of the things I loved about your book, and really about a lot of the writing that you've done, and the speaking that you've done is you are a great voice for talking about career progression. And I think you have lots of interesting things to say about that, and would love to just dive in, and start with that topic. So, one of the things that I think is true of today, careers today, that was probably not true 10, or 20 years ago is, as I always say, careers used to be like ladders, your next job had to be the one above yours. Which meant you had to wait for your boss to get promoted, or quit, or get fired, or retire, or something. And that today careers are much more like jungle gyms, and your next job is anything you can grab. It's anything you're close enough to. It doesn't have to be the thing right there, but anything you're close enough to that you can grab, and add value in different ways. And I'd love to hear from you some of the more sort of creative career paths either that you've been through, or that you've seen others go through at sort of the mid, and senior levels, and startups, and how those work.

Sarah E. Brown: Great question, title, or subtitle for the book was almost the non- linear path when we were talking with the Wiley team because to your point, it's absolutely non- linear for most startup leaders. And unlike at larger companies, or even later stage startups, once they've built career pathing, a lot of startups have, to your point, many different opportunities for startup folks that's not necessarily written out in a guidebook. And so as startup employees, and something that really got me interested in writing about this topic, and learning about this topic, for my own edification, we really have to figure out a lot of this on our own. And so some of the career paths I've seen have been really looking at how to get to what's right for you, which may, or may not be quote, unquote, the next rung. So, for instance, coming up, for instance, in startup marketing, many people get siloed into a particular area of expertise. They start out as a generalist, but then they're the content person, or the demand gen person. And to really lead the function have to have an understanding of all of the parts of marketing. And so in order to get that expertise, we see a lot of folks doing things like consulting, or potentially asking for a project that's outside of their remit on a day- to- day basis while still handling their day- to- day job. I'll give an example. I had an employee at my company where he was a generalist. He started, I think he was marketer number one, very, very early on, and was doing the ads, and the landing pages, and all of that, and became really obsessed with our brand, and working on brand topics. So, when he took that on, he was able then get promoted into his first management role by really seeing a need in filling that. We see that in the startup world. Also, someone on my team who came from the product world. Really awesome product person became a product marketer, right? Natural fit. And we see a lot of different versions of this. So, I'd say if you're looking for startup leadership, also if you're at a big company, and you want to come work at a scale up, I just spoke with a woman who's head of RevOps, was at a large company, and wants to go into the startup world, and she said, " Sarah, I think I'm going to like it, but I have no idea. What's the startup world really like?" And I said, " It really depends", but we talked about what could be helpful for her in her process of getting her first startup leadership role coming from a different direction, and she's going to also try consulting with a potential full- time opportunity at the end of it to see if it's a mutual fit.

Matt Blumberg: Yeah. People's careers are just so fluid, and so different now, and it used to be which if you're looking at a resume, you hire people all the time, too. You look at a resume, and someone was at this string of things for two years, or three years, or 18 months, you'd be like, " Oh, what's wrong with them? Why haven't they have been somewhere for a long time?" And I think now you look at that, and yeah, maybe if there's too much of that, you want to ask a couple questions, but a lot of the time you look at that, and you value the variety of experience.

Sarah E. Brown: I think that's true. And people who have stayed at a company for a long time can do really different roles within that. I remember I was acqui- hired, so I was head of marketing for a really tiny product, and we got acquired, and then my role became much more generalist. This was much earlier in my career. And when I was then marketing 13 lines of business versus one, I had to learn a whole new set of skills. There were different ideal customer profiles that were target markets we were selling to. And so I also think if you're willing to hang on at a large company, or at a company that's growing, and to your point being willing to be maybe title agnostic, or care less about the sort of next rung, and take a lateral move, quote, unquote, but that's going to teach you something new, it can open up a lot of different possibilities. So, that certainly was true for me, and I've seen that with others as well.

Matt Blumberg: Yeah, I think there's so much value to the company. There's obviously value to the employee to move around, and get skilled in different disciplines, different roles. There's so much value to the company in retaining top talent that might otherwise get itchy to go somewhere else if the job above is not available. If you can move top talent around from product management to marketing, from marketing to sales, from engineering to product, whatever the move is. And we always found at the scale that we got at the end of Return Path, we were about 500 people. We were moving about 10% of the workforce every year, laterally, and from one department to another. And we just got huge value out of that. And we decided at some point that training someone in the company when they were a functional expert from the outside was just as hard as training someone in the function, but who had the knowledge of the company, the products, the customers, et cetera. So, I think the value to the company is real, too. All right. So, one of the other things you talk about in the book that I think is such a great insight is the struggle of the big company executive that gets hired into the startup. And every company goes through this. At some point you're in a board meeting, it's almost always in a board meeting, and someone on the board says, " It's time to hire the adult supervision", or hopefully something a little less pejorative. It's time to bring in someone who really knows what they're doing, and pick your function. And I don't have data on this, I would guess the majority of those hires don't work. And I remember one that one that we had early in my career when I was running, I actually wasn't even an executive level yet at Movie Phone, the company I was at for a bunch of years before I started Return Path. And the company hired the adult supervision to run marketing. And this is the mid nineties, so you have to remember as you hear the story, and the person came in, and he had had a 20 year career in CPG marketing. He was an incredibly nice guy, and very good at what he did. And he came in on the first day, and he asked where the typing pool was. And obviously there's no such thing as that anymore, but there was not a lot of that even then. And that's the environment he came out of, he came out of an environment where he was surrounded by support staff, and surrounded by help, and his assistants had assistants. And even today when people are a little more self- served, dropping someone like that into a startup can be incredibly difficult for the person, and for the startup. So, how have you, that was a long wind up to the question, but how have you seen that work? When it works, why does it work? And when it doesn't work, what's the early warning sign?

Sarah E. Brown: Great question. Yes, the march of the incoming execs suite, we've been there. I've been there, and I think, so startup, CEO Erin Rand, who's quoted in the book was at a large company brocade for a long time. And when she made the switch to the startup world, I think one of the biggest challenges she noted was the political differences, and how things get done. It's not a memo, it's not a PowerPoint presentation, it's go do it, and maybe talk about it in some form, but really a bias towards action. And I'd say the turnaround for decision making had to be really different than what she was used to. And there were also a lot of different cultural things around sharing one's personal life. I think in the startup world, ostensibly were expected to be more maybe closer to folks, and not necessarily have all of those hierarchical pieces, especially earlier stage. And so she had to, I think she called it get the corporate off her, or knock the corporate off her. And so there were, I would say, advice for someone making that change. And having recently spoken with someone who's been a leader at a larger company in RevOps, and has recently decided to move to the startup world is really understanding if you are willing to be in those cultural environments where speed, and communication are different, and being willing to potentially go back into the weeds if you've been really removed from it, and whether you're joining an early stage company, or even a later stage company, I think you really have to have more of an understanding even you're not executing, of course you're hiring a team. Being willing to really understand that the granular level what's happening. Whereas at a larger company, a lot of that's already sort of the status quo is performing, and you're coming into potentially manage things differently, but you're not building something necessarily in the same way. And then I think a pitfall I've also seen is this idea of command, and control. We've seen leaders come in from larger companies, they're used to whether, or not they're looking for some typing pool that does not exist. This idea of it's my way comply. I think today's modern workforce in general struggles with that, but particularly I think who's attracted to work at a startup, people who want to experiment.

Matt Blumberg: No, startups are about, " Hey, let's go together over there, and let's figure out how to go", as opposed to like you go there now.

Sarah E. Brown: I also think it's interesting depending on the function, I've seen big company folks really struggle to hire because they don't have a sense of also the persona they're looking for with talent. So, really, I would say spend a lot of time with your HR team, with your talent team to really define who your ideal candidates are, because as you're building your team, you don't want to hire people who would've succeeded at your previous company. You have to hire a different profile who will support you.

Matt Blumberg: Yeah. Well, and it's interesting that your story about who was an Erin that she said, " I have to knock the corporate off of me." So, as with most things in life, self- awareness is the key to lots of good things including change. So, assuming you're a startup person, someone gets hired into the seat next to you, or above you, and they're super corporate, and let's assume that they have that openness. That they're like, " All right, I got to do things differently." How do you help them? How do you help them as their peer? How do you help them working for them? How do you help them as their boss?

Sarah E. Brown: Perfect question. I think helping people understand the importance of really getting on the shop floor, so to speak. I know you're used to this, working a certain way at a different company might be going through your head, but that doesn't necessarily resonate. You have to help someone understand this thing that you think should be running this way, we actually don't even have the software yet. I think really testing your own assumptions with what a person would understand that they... I think they expect usually with a leader who's coming in from that background, they expect a lot of things that don't exist yet. And so I'd say help them size their expectations by showing them data, showing them, here's what we have, and here's what we're building. Help me understand how to help you with your vision, because the execution is going to look different than at your previous company. And an example of that is I was at a company where the sales leader came from a really large company, and he said, " Okay, it's time for SKO. Where's the assistant who can help organize all of this?" It's like, " Nope, first SKO? You've got this."

Matt Blumberg: I'm so sorry. Yeah.

Sarah E. Brown: And to the point of this leader, she did a really good job of building a really awesome first SKO at that company, but it was a mindset shift of there's no one who's going to set this up for you. And even, yes, you're going to have to book the conference center, and you're going to have to find someone on your team who can research what activities are happening, that level of detail. Whereas you would hire more people who would own all of those things. So, really surprising what things you have to do on your own unclog, the proverbial toilets so to speak,

Matt Blumberg: Or maybe even the real ones.

Sarah E. Brown: There you go. And I'd say also just advice if you're working with someone who has a really different mindset is find that relationship early on, especially if they're coming from a culture where maybe you have to watch your back a lot, or there's, I'd say, politics, and I've actually worked with folks who at different levels of seniority have come from larger companies where there is a lot of, I'd say proactive defensiveness that it slows things down. And at first it was weird. I was like, "Well, why is this person doing this?" And then I had empathy, and realized, " Oh, it's because of their last company. People would take credit for this idea, and then their department didn't get this funding." I mean, it was very weird. So just this, yeah.

Matt Blumberg: The politics are really interesting topic, and it's not that all big companies have a ton of it, and all startups don't, but I think there's a correlation between amount of politics, and size of company. I don't know what the R squared is, but it's decent. We had someone that was a senior exec on my team many years ago who was totally ineffective, totally qualified to do the job, totally ineffective. And when either he quit, or I fired him, and I think I ended up firing him, he got very huffy, and he said, " I could never figure out whose ass I had to kiss to get something done around this place." And I remember after he left thinking, " Yeah, he never figured it out. There was no as to kiss, he actually just had to go do the work." I don't know how you reprogram someone who's used to that kind of environment, where the way you get something done is finding the right ass to kiss. I could never get my head around that.

Sarah E. Brown: I hear you. I'll frame this all a little more positively ... focus on the strength of this big company person who was brought in because a board member, or someone decided that their expertise would be valuable. So, lean on what they do bring. They may, or may not know how to look at Salesforce properly, and they're so used to someone else handing them a dashboard that already has everything explained. They're not going to know necessarily what to ask for. However, you hire that chief operations officer from that large company, and it's time for your first board meeting. Be very grateful that they can clean up everything before that board meeting. Actually be able to make the startup look way more advanced than it is. And so figure out what those strengths are, whether it's their background, or something that they've done for years, and leverage that. And I'd say be patient with their learning curve as patient as possible.

Matt Blumberg: That is probably the only thing you can do. So, that's a good way to think about it. One of the phrases that I think you, and I both use, and I think you had it in your book, is around getting promoted by just going ahead, and doing that next job that you want to get promoted into anyway. And I think you, and I both use the language of just act as if you have it. And obviously you still have to get your current job done, you have to get it done really well, but you just literally just start doing the next job, and eventually you find yourself in it. And I've seen this work really well. I've also seen it prove to be problematic from time to time, not because someone's stepping on someone else's toes, but more that there are CEOs, and there are leaders who really get anchored on their first impression of someone. And when someone starts as an EA, and then gets promoted into a marketing coordinator, and then gets promoted into a manager, and 10 years can go by, and the CEO still thinks of that person as the 25 year old, or 23 year old who showed up as the EA, how do you fight against that when it's you? I mean obviously the one way to fight against it is you leave the company, and you go somewhere else, and you've got your title, and experience, and maybe you come back someday, but how do you quietly gently, or not gently, and quietly work that through an organization?

Sarah E. Brown: It's a struggle. It's a struggle. And I'm not going to have the best answer here, but I will say from my own experience, I think sometimes you really do have to leave. That's real, because to your point, people have perception solidified. I think this idea of moving to a different part of the company at least can be really helpful. If you're known as the customer marketing person, and suddenly you're wanting to do sales, people are going to ask you about customer marketing, and you're always going to be known in some way for that in a organization. I think struggle for, I'd be curious to hear from EAs who sort of are still being asked to schedule things 10 years later. It's like, " No, no, that's not what I'm doing right now." So, I think good boundary setting of course, and sort of reminding people. I will say one challenge in kind of going for the next rung, or taking something on is have a really clear conversation with your manager, with your CEO about what success looks like in that next role. And you may think, " Oh, I'm, organizing the sales team birthday parties. Samantha McKenna, former VP of sales at LinkedIn said she had people on her team saying, " Oh, I, organized the company social hour, and so I should be a manager." And she said, " Did you hit your quota this quarter?" You still have to hit your quota. And by the way, organizing the company birthday is not necessarily what she looks for in a sales director, or whatnot. And so saying, " Well, what does success look like?" And if your startup hasn't built career pathing, figure out some proxy for that. Also, I would say if you're looking for a certain role that maybe isn't available at your current company, doing fractional consulting with Bolster with another organization is really helpful because there are certain parts of the job that you know can take on a lot on your own in addition to your current job. But until you've built a budget, you're not going to necessarily have to if you have someone above you who's already doing that. And so find a way to do that for someone else, or find some piece of your role where you could expand it to the next layer without necessarily doing it at your current company. Or if you're going to do it at your current company, make sure there's room for it, to your point on stepping on toes.

Matt Blumberg: Well, and that's probably a good topic to another thing I wanted to talk to you about for a couple minutes, which is sort of the concept of sponsorship, or mentorship. And I don't know how you define those, and if you define those two things differently, or if you have some other framework, or construct, but I have been the beneficiary of really strong mentorship in my career. I have tried to pay that forward. I've tried to create organizations that I've worked in that sort of do that systematically. Quite frankly, the whole premise of Bolster is to bring that to the startup ecosystem externally. But how do you think about that internally at a company, and how do you think about it from both perspectives, both your early career, mid- career, and you need sponsorship, or mentorship, and your company doesn't do that systematically. And then how do you think about that from the perspective of a leader if you're in an organization that doesn't foster it?

Sarah E. Brown: Great question. First I might put you on the spot. Do you want to define how you see the differences? Because I know we've talked about this a lot, the mentorship, sponsorship, coaching trio.

Matt Blumberg: So, and I think hopefully I have the same answer I had last time, which is I have a clear difference in my mind between mentor, and coach, and I don't have as good a definition of sponsor. So, for me, the difference between coach, and mentor is a coach helps you be the best version of you, as a human. So they work with you on things like are you a good listener? Are you a clear communicator? Are you being true to your values? Have you defined your values? How do you show up? And a mentor is someone that can help you learn your job, right? They've been the CMO, and you're not the CMO, they've been a CEO, and you're taking that job for the first time. And I guess if I had to define sponsor, and now I'm way more curious to hear your definition of it, because it's probably a lot better, it would be someone who's helping you navigate the organization that you're in.

Sarah E. Brown: Super helpful. No, I love those definitions. I think kind of getting at the heart of your question of how do you find mentorship within your company, and to your point, you may, or may not have a former CMO floating around unless it's the CEO. And even then that person probably has limited time. I like Sam Jacobs Community Pavilion. There's Bolster, there's organizations like Chief where you can find either peer mentorship, or folks who have had the job before in different capacities, and potentially are willing to support you. If you go through an accelerator like Techstars, right? Founders get access to pools of mentors. I think one of the challenges with coming up in your career is it's hard to figure out what a mentor needs to be like. Do you just find someone who's more senior, or someone who's really good at a particular skillset that you don't have yet? And I think it's always helpful as you're looking at what you're trying to accomplish, and what your outcomes you're trying to achieve as finding sort of the guides who will support you on your path. And that can be sponsors who I don't have a great definition for it either other than I'd say people who are supporting you to your point within an organization, but also I think particularly cross- functionally who will champion your work. And something that I talk about in the book lead upwards a lot is your quote, first team is really your fellow startup leaders, your executives, it's not necessarily your functional area that you're owning, and figuring out how to work really closely with your CFO if you are a VP of sales, or CRO. How to work really closely with your engineering team, and from product team when you're in operations, or customer success, and making sure that all of the different cross- functional sponsor sponsorships for your programs, especially as you're growing your company, things like customer success, and sales, they need to be tied at the hip. And thinking about retention is now something that in today's difficult fundraising climate, I know a lot of founders are thinking of. And so this would be my advice to founders, too, is encourage your teams to really build those strong relationships, whether it's through regular offsites where you're encouraging intra team bonding with your first team, but also encouraging people even in a remote setting, or hybrid setting to find the time for those relationships. Because I think a lot can get lost, and it slows an organization down a lot. I really value taking extra time with my peers. I think that's also a competitive advantage when you're going to market against competitors where they don't... We've all seen when sales sells something, customer success is like, " What the heck did you do?" And inaudible

Matt Blumberg: ...with me?

Sarah E. Brown: That's not in the product? What are you doing? We can't put that on the roadmap. So, in all seriousness, I think the next sort of wave of companies that are really focused on net dollar retention, and success, they're going to have those really tight cross- functional relationships, particularly on the revenue team, but also on I think the entire customer life cycle.

Matt Blumberg: Yeah. No, I think that's probably right. And so I want to build on something you said there that I think is interesting. So I'm a big reader of Patrick Lencioni, and I think this sort of first team concept is pretty prominent in some of his books, and it's certainly something that I, as a CEO, I'm always pushing with my leadership team. No, no, no, this is your first team. You cannot show up here as the delegate of the... The head of the marketing delegation. You're here as a senior executive. This is the team that's steering the whole ship. I haven't given thought to what that's like one layer down, because I haven't been a CXO in a very long time, and I was probably a really immature one when I was, and a lot of this literature, and thinking kind of hadn't evolved yet at that point. So, you as a marketing leader, do you manage your marketing leadership team that same way, and you tell them all like, " No, this is your first team. You can't come in as the representative of brand, and you as the representative of product marketing." And does that translate down, or does it get watered down?

Sarah E. Brown: I haven't had that explicit sort of statement come out of my mouth, but yes, I think that's the sentiment in that particularly as we're working cross- functionally, and there's, I think, startups now titles. I mean we have all kinds of titles that happen in startups, but we see people, product marketing can live in product, and it can live in marketing, customer success, account management can live in CS, or sales. I think there's certain areas of the business that are more clear, but for a lot of companies, like ownership has to be defined. Who's incentivized for renewals? Is the CS team, or sales team, or some combination. So, I think what I want to share here is as you're building your team, and you're thinking about it, remembering sort of the why, like why are you, organizing in a certain way? And so when I think about the first team management part of what I know is that we all have more context about everything cross- functionally than everyone on our sort of individual departmental teams. So, it's interesting, you're both a delegate to your first team, which is that executive layer. And there's certain things you can't share, or can't share yet with your department. And at the same time, you have all the context in your department that your first team doesn't have. And so sometimes I feel like I'm constantly communicating up, and down in that way, and also filtering with discretion, and certain information that I can't necessarily share. And I think one of the most frustrating things as a startup employee, or someone coming up through the startup world is this decision is happening, and I don't understand it, just in general. And so the more that we can help people understand, even if they don't agree with why decisions were made, and have some sort of thing that they can point to, that's really helpful. And again, it's helpful both with your first team but also in a department.

Matt Blumberg: Yeah, I think that's a really good way of framing it. And I think it's tough. I have a lot of admiration for people who are CXOs, because more than the CEO, you really are in two different worlds. Yes, the CEO has a board to manage, and CEO is also part of two teams, but that that's not the same. And look, the bigger the organization gets, that just cascades down. Your direct reports will have their own large teams to manage, and they're missing context from two rungs of them.

Sarah E. Brown: Absolutely. Absolutely. And it's great. Anyone who's ever run an ads account, right? Oh, my gosh, the amex broke, right? That's an immediate issue, and you have to switch cards, or things like that. These little things break, but they can shut down an ad program for a day, or for a few days. And I'm giving this example, because I think about the times when your team suddenly needs to be exposed, they need that support from you. They need you to champion something within the, organization, get with the CFO, figure it out. Yeah. Oh my gosh, we just opened an entity in Spain, and suddenly we have this new bank account in Spain, and make sure people are hired appropriately if they just move to Spain. All of these things come up, especially, if you're working in international company. And I think one of the most important things is empowerment, empowering your team, but also there are certain things where you as the leader, unfortunately, you're the only one who can sort of zoom to the next thing, and get people connected to who they need to make the thing happen. So, I think being very humble about that. And yes, not above unclogging a toilet, not above getting someone amexed ASAP, and just like a CEO, right? I mean, you're fixing these things, too.

Matt Blumberg: And I get those, the doing that can be very frustrating to the people on your team because they're like, " Hey, why is this person swooping in, and doing it? Why couldn't I do that?" And the reality is sometimes it's just easier. It's easier for the CXO to do it than a manager, or it's easier for the CEO to do it than a CXO. inaudible

Sarah E. Brown: Oh, go ahead.

Matt Blumberg: Go ahead. No, I was going to say last question. Although, we can have you back again, and I always love talking to you.

Sarah E. Brown: Thank you, Matt. Likewise.

Matt Blumberg: Let's talk about quitting.

Sarah E. Brown: I'm so happy.

Matt Blumberg: What is the right way to quit as an executive?

Sarah E. Brown: I'm smiling, and I'm excited not because I love this topic. I mean, it's just so juicy, and I think I'm really excited because Matt, I really resonate with your perspectives on it, and something, not to put words in your mouth, but I've heard you talk about in the past sort of this idea of maybe a leader coming to you before they've made the decision. And I was, as was preparing for this delightful conversation, I knew it was going to be delightful, or I had had a strong feeling yesterday, and I was thinking about it. I realized this is one of the key moments in a startup journey where the founder really has very little control in some ways. If someone has decided they want to move on, but you desperately want them to stay, or need them to stay even for a given time period, suddenly the power is imbalanced. There's a shift. And so my advice for CXO is, first of all, if you're in your first startup leadership role, no, you can't give two weeks. Don't do that. That feels inhumane, and ...

Matt Blumberg: ...practice.

Sarah E. Brown: Yeah. I mean, in certain countries I think that's illegal, or I don't even know. It's definitely not standard. But in the US we have at will employment, of course. There are a lot of different circumstances, and I'm sure there's exceptions to this, but in general, and I give an outline on how to do this in the book lead upwards is I'd say at least come up with a timeline that enables you to do your job successfully, and manage the transition well, knowing that you couldn't possibly hand off an entire program in two weeks, that's unrealistic. The second thing is really decide, are you really sure that you want to move on, or is it still fixable? Is there some piece that could potentially be workable? And this is advice I give very candidly. I mean, this is a complicated job market for a lot of reasons, but you have to be willing in certain cases to potentially close your laptop, and have it be your last day when you have the conversation. That's never happened to me personally, but I've heard of it happening to folks, and we've all seen folks who've been let go, and it is just their last day. If you haven't done a great job, maybe that's fine. Closing your laptop is fine. But if you're doing a good job, if you want to do sort of shepherd your team, if you have health insurance things that are tied to your family's security, it's aiming thoughtful of if someone were to say, worst case scenario, close your laptop, you're not unaware that, that's a potential, hopefully that won't happen. And then also going into the conversation, understanding what you're willing to do versus what your ideal case would be. And so...

Matt Blumberg: When the CEO says, " Yeah, oh, that's terrific. A 12 month transition sounds awesome."

Sarah E. Brown: Yeah, 24 months sounds great. Yeah, I mean, I've stayed longer at companies than I've wanted to. I'll be honest. There was a job I wrapped up where I was in a leadership role, and I knew the company was getting acquired, and it was the right thing to do for my equity for a lot of reasons that were selfish, not just for the sort of altruism of it, but I wanted to make sure that we hit our targets, because this acquisition required a lot of different pieces to be in place. And I was a part of that, of the revenue team, and I had hoped to wrap up after two months- ish, ended up staying I think four. It was fine. And my new role was willing to wait, and we had good communication there. And I also think a place that really wants you, and understands your value will hopefully be willing to work with you.

Matt Blumberg: Absolutely. And willing to have you take a vacation before you start.

Sarah E. Brown: Absolutely crucial. I love that. I also say when it comes to quitting, too, I mean you have to decide how much you're willing to disclose. And I'm curious how this lands for you as a CEO, but I think it can be hard to give certain feedback. And also if you're holding on to so much feedback when you're leaving, there's probably been bigger issues along the way. I mean, ideally. Ideally, you're not running from a company, you're running towards what's next, and exciting. Again, this is a hard topic. I'm very open to feedback. I'm curious how you think about this as a CEO, Matt, maybe as we wrap up.

Matt Blumberg: I love getting exit feedback, and sometimes you know what it is, you're not surprised at all. Sometimes you're surprised. And I've always been really disciplined about getting exit feedback. I like collecting it myself. If I recognize that a given departure is a little fraught, I will have HR do it, which they systematically do. Or I'll even have a board member do it if an executive leaves. So, I think it's a gift.

Sarah E. Brown: Cool. I'll share one more note, which is I think endings are really hard in general for people, and people inaudible

Matt Blumberg: My line on that is if things ended well, they wouldn't end.

Sarah E. Brown: Okay. Yeah, that's definitely a viewpoint. Look, people pay attention to how people leave your company. And if you're an executive, and you leave in a hurry, and it's this dramatic thing, first of all, any team members you ever take with you, that creates bad will, right? If you ever were to recruit from your previous team, that people have that in their memory. And I also think it scares other executives, too. And I think it just puts everyone on edge. So, one thing, I work for a European company, people will be let go, and stay on much longer than you would expect based on labor law. And so there's a culture of almost like, we know this person is done, but they're going to spend a month wrapping things up. And to me it feels like mutual respect. Sometimes you have to really exit someone from the business. But I think the spirit of this person has provided some value, and we want to honor them. I would say regardless of how things feel inside, potentially very stormy, try to leave with as clear of a head as possible, not burn bridges unless you have to. And to the point, if you have equity that you are thinking about exercising. A lot of people do negotiate longer windows than three months, inaudible but that's part of my closed laptop thing is, again, it hasn't happened to me personally. I've heard of it happening to others, is are you willing to put up cash within three months if you want to buy your equity, and you work for a US company, or that's the structure. So, things to think about.

Matt Blumberg: All right. And on that note, I think we are going to close today. I will have you back on, and talk more at some other point, but Sarah Brown, author of Lead Upward, CMO extraordinaire, thank you for being here.

Sarah E. Brown: Thanks for having me, Matt.


Today’s episode is a deep dive with tech marketing expert Sarah Brown. Sarah is a startup mentor, ecosystem builder, and the author of Lead Upwards.

She and Matt discuss creative career paths—Sarah considered “The Non-Linear Path” as an alternate title for her book—and the unique opportunities startups present. They also share their thoughts on the contrast between startups and large companies, from office politics to overall function.

Tune in to hear about mentorship, team hierarchy, and Sarah’s take on quitting as an executive.

Today's Host

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Matt Blumberg

|Co-Founder & CEO, Bolster

Today's Guests

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Sarah E. Brown

|VP of Marketing, Sastrify