B (5:40)

That's great. Yeah, I really appreciate that story. One thing that I'm thinking about as you tell me this is just the connection points as you pivot in your career. For me, I have similar transitions where I work for the Department of Defense, did some entrepreneurship for a while and then broke into vc. So with me, looking back, I can see some connection points. What are the connection points that you see being in banking? Those quantitative skills and then how do you see that kind of tying together those superpowers that you had from banking to entrepreneurship to public policy and now into venture capital? Obviously with running for Congress, I'm assuming you probably have to raise a lot of money. So I'm assuming your experience being an entrepreneur, raising money, storytelling, what are some of the connection points or skill sets that you've seen kind of evolve and translate to complement your journey?

A (6:41)

That's a great question. And I think the fundraising point is a really critical one. I often joke socially that I spend my life raising money to the extent that my university, I went to Yale and I was an athlete there, and we're building out the Yale women's athletic network. And I said, I'll do anything for this group except fundraise, because I spend my entire life fundraising. And then they said, oh, thank you. Well, we'll put you down for a head of fundraising.

B (7:08)

Wait, what?

A (7:09)

But yeah, I mean, fundraising is a tool. It's a skill that's important because it allows for the deployment of capital into things that are productive for society. I think on the investment banking and private equity side, I sort of learned early in my career the fundamentals of finance and also just of being a professional and a businesswoman. I was a history major in college, so I, you know, that foundational experience was very important for me. And then in my business, you know, fundraising is just our lifeblood. Got to manage cash and pay the bills as an entrepreneur. So raised a lot of money. There is about seven rounds of financing from the seed round through a series C. And that enabled us to grow the business, buy other companies, consolidate the industry, drive best in class growth, and then in politics, you raise a lot of money as well. Unfortunately, that's still our political system. So spend a lot of my time doing that. And then the funds I'm working with, two of the funds are now out raising money Impact venture capital, where I'm a venture partner, which is an artificial intelligence focused fund based in California. We invest across the US but we are based in California and we are currently raising a hundred million dollar fund too. And I also advise a fund based in the UK called Eight Dimensions Ventures, which is a health and wellness focused fund. We call ourselves ESG because we apply the eight Dimensions framework, which is a scientific methodology that looks at wellness of people and planet to score our investment opportunities. So top venture returns, but ensuring that the investments we do also do good for people and planet. So those themes are really prevalent. I think, you know, in order to raise money or in order to build a business or in order to bring people together behind you in a campaign or as an entrepreneur, you do need to be able to tell a Story to show passion to, to excite people. Because whether it's a startup or it is a campaign, it's a lot of work. Often you're paid in other ways than a big glossy cash salary. And that is a critical, critical skill. And often joked in my campaign, it literally was another startup. I mean, so many of the activities were the same as starting a business and then raising funds. Even though I'm more operating on the part time advisory context right now, you know, it's still another entrepreneurial experience.

B (9:56)

Yeah. Any, you know, any advice you have for, you know, first time fund managers to build relationships with LPs, I think we can both agree. And I always say this too, I mean, I think sales is the most important skill in life. Like, I mean, whether find a life partner, whether you're trying to get a job offer and you know, be the best candidate. I always believe sales is super important. But you know, we've been talking about kind of these emerging managers coming in and then people that are on fund too. What are some tips that you would give? Kind of looking back on just fundraising as a whole, maybe in general as an entrepreneur, and then what are the differences that you've seen on the fund side with fundraising and just kind of, you know, really building relationships with LPs?

A (10:42)

Yeah, that's a great question. I mean, it's really interesting and could answer your question directly. But just a slight tangent. I spend a lot of my time on the advisory side and this is both through the funds I work with and then on the direct side working with entrepreneurs who often have a great idea, a great technology and capital behind it. If we look at the world today, there's a lot of capital and there's a lot of great ideas and there's a lot of great entrepreneurs. I think the companies that succeed really figure out how to take those things and build a go to market and a growth plan. Who buys it? Who's our ideal customer? What's the staging of this? How do we fund this through the journey? How do we set the milestones to drive the investment conversation? That is actually the same for funds. Right. There's a lot of people raising funds, there's a lot of people with great ideas, great theses for their funds. There's not a lot of people that know exactly how to position their fund, how to articulate that in the market, have a plan, execute that, and then ultimately bring in the capital and close the funds. So the advisory work that I do now really hits on those two areas. It was my expertise As a entrepreneur, I led all of the sales in our business and the go to market growth, fundraising, strategic activities. My co founder was leading our product and engineering and operational organizations. So that I think is just an absolutely critical skill, whether you are raising a fund or you are building a company. And what I find so interesting is I have so many companies that come to me asking to contribute that expertise. And I also have so many funds that come to me saying, oh my gosh, we just put all this money into all these companies and we need to go to market plan. Which is an interesting question of chicken or egg. So that I think that I just want to hit on that because that's what I'm seeing so, so prevalently in the market today. I think with respect to building those relationships with relationship building, stakeholder management, sales has a lot of themes, whether you're an investment banker, you're a politician, you're an entrepreneur and doing, you know, enterprise sales, or you're a GP raising a fund. And I think it starts with, fine, you know, it start. This is going to sound very basic, but it starts with research, like, am I talking to the right people? What have they done in the past? Why would they care about this, et cetera. Then it goes with building a relationship. You can't just pick up the phone and ask someone for money. I always advocate a direct introduction, whether you're a CEO or raising a fund. My experience has been it's incredibly rare that a cold outreach results in anything. It's a direct introduction. It's meeting someone at a conference and nurturing that relationship or through an existing network. It's spending a lot of time on your LinkedIn feed and figuring out who knows whom and who can make that introduction. And then I think it really is down to having a compelling thesis for your fund that differentiates you in what is very much a crowded marketplace today of people raising funds. And then down to back to that point of how do you then position that idea, how do you make the materials, how do you articulate that, how do you drive the process from an execution and data management perspective? And all of those things contribute to successful fundraising and incidentally also successful go to market plans and sales and any other aspect of a business, whether it's at the seed stage or the series D stage.

B (14:35)

Any best practices for the layers of the collateral and then the follow up? Because I've spoken to a lot of people that have been in our emerging manager program and obviously sometimes you start with a one sheeter, maybe you have an abbreviated Deck, then you have a detail deck, you have a diligence deck. And then there's a cadence for kind of like follow up and finding interest. So any tips that you give your clients as far as kind of the cadence and maybe the high level layers of information because obviously you don't want to give them the whole data room the first day. Right. You want to give them maybe a teaser, one sheeter. I guess the cadence that I expressed with just those different layers, does that resonate well with some of your strategies that you've recommended or are there other ideas that you have as far as just kind of, just kind of providing the materials?

A (15:30)

Yeah. From a materials perspective, I think it's critical to have really three things. The teaser. So it can be a one or a two pager, but something that is, can capture people's attention and as I said, get them on the phone, people want to default to email, people are busy, you know, get them on zoom to get the full story to build the relationship or get them now that things are opening up more, get them to a coffee. Right. So you can forge that connection. So that's really the purpose of the teaser. And then the second thing is a deck. I very much advocate for doing the work to make your deck as concise and clear as possible. And then having a lot of supporting information in the appendix. Most people should get it in advance of the first meeting for a pre read. Most people are very busy. Most people aren't going to flip through 15 or 20 slides. You know, the best practice is sort of 10 to 15 and then you can reference a lot of data or a lot of supporting information in the appendix. And then the third, and I think the deck is the most important piece of this, you know, really doing the work on that. And then the third piece, which again is the most important. So I probably said that incorrectly, but the deck is more important than the teaser. Then you have the data room and that is all of the information about the fund, the fund model, the bios of the gps in more detail, information on prior investments, if that exists or what's in the pipeline, if it's a newer fund and everything that goes around that so that an incoming LP can get confidence in the GPS and the quality of thinking and materials and get confidence through their due diligence in making an allocation to the fund. But it's really important, I think, to do the work in advance of those things, refining the thesis of the fund. I think that this is often overlooked in this market. I mean there are so Many people raising funds that sort of go like this. The startup space is really hot. I've been a great finance person or I've been an operator. I'm going to raise a fund and that just isn't good enough in a market where so many people are competing for capital and so many existing funds are pulling up their timelines for raising new funds. So I think having a thesis, whether it is like in the case of Impact Venture Capital, where I'm a venture partner, our thesis is AI is going to transform the world. It's already doing that. And applying it to finance health care and cybersecurity is an area where we can build really big companies and generate outsized returns for our LPs. That's a very cogent, focused thesis tied to an emerging technology tied to specific industries. In the case of Eight Dimensions Ventures, it's the health and wellness industry is a $4.5 trillion industry. It's three times the global pharmaceutical market. And investing in health and wellness will do good for people and planet. Big businesses do good. But I think, and so developing that and then making the materials that position that I think is really critical in a market in particular where there's competition for capital.

B (18:53)

I've got another question for you. So just kind of a minor question. This is more around etiquette and I'm only bringing it up because it came up in our accelerator, in our emerging manager accelerator. So I give everybody my link to calendly, like even LPs, and I love it because I magically see the calendar show up. So I don't really think too much of a formality about it. But I've seen a few emerging managers actually handle scheduling with LPs a little differently. They'll actually just manually try to find the times that work for LPs and they'll kind of just manually do it on the calendar. And I don't know what your thoughts are on that. Is it. Is it bad to just give everybody your calendly? Because it is kind of. It kind of is an inconvenience when you got to use somebody else's calendar, right? Because you got to like match up their calendar with yours. So any thoughts on that or does it matter? Just, just wanted your. Your opinion.

A (19:46)

It's an interesting question. It's funny that you bring this up. I was just thinking about this yesterday with a business that I advised that does enterprise sales that is operating in this way. To be honest, I've never done that. I am, I guess maybe old school. It does Take a phenomenal amount of time to schedule stuff. I feel like my day doing scheduling and miss my incredible assistant Sophia, who was like my right hand and dearest friend for many, many years at Topia. So, so much every day. But you know, my viewpoint is everyone is looking for a reason to say no. Right? I mean that's, I think the lens, it's a little bit of a pessimistic lens, but that's the lens that you have to look at. Sales, political fundraising, fund fundraising, you know, with. Right. People are busy, a very, very busy. And they're looking for a reason to say no to you. No, I don't want to take a meeting. No, I'm not going to invest in your fund. So your job as someone raising money or doing sales, raising a fund is to make it as easy as possible for them to say yes. So not give them any out any canned statement that they can say back to you. So my perspective is that I would personally not use calendly or not advise people to because I think that that just creates a barrier to your point.

B (21:10)

They have to go in, they're clicking out.

A (21:12)

Burden of scheduling, you know, rather than just saying copying Sally and she'll organize it or copying my assistant Joe and he'll organize it. And I think that that's just one thing to be cognizant of. Also the, you know, there is a little bit of a generational aspect to this perhaps. So I think depending on who you're talking to, it may be more or less accepted. But I just assume that going with what people are comfortable with in the masses is a more seamless course of action. This may have changed. You know, people are getting more adopted or adopting calendly more getting more comfortable with it. But you know, I just again always try to reduce barriers and make things as easy as possible and as sort of standard operating procedure as possible for lp.

B (22:09)

And if you don't have an assistant, I guess maybe just in clear bullets, just list your time slots that are available and ask. And I know it's like so simple to like, but I'm making it more complicated. But is it, you know, so when you do it, let's say you don't have an assistant, right. So you just ask them for the time slots that they're available for and then, and then you just kind of book a time or do you give them your time slots as well?

A (22:32)

Or what I typically do is say like to schedule a call, I'm available this these times next week and then like Monday x to Y Eastern time, Tuesday, X to Y and just go down and say, is there a time that works for you? I mean that's one way to do it. The other way is just depending on how full your calendar is or how much of a priority the person you're emailing with is, is to just say, you know, please suggest sometimes that work for you and then you are the one that fits that in.

B (23:07)

Yeah, I think it, I think the earlier one is less burdensome for them because they don't have to hold those spots and they, you know, so I think they can just kind of look at their calendar really quickly and respond in the email versus calendly. Like, like you noted, like you noted earlier, you're kind of clicking out from the experience and I know we're, we're spending too much time on this, but it's these minute details that I think people pick up on and it's something that I've been recently noticing. So, you know, thanks for sharing your opinion on that.

A (23:37)

Sure.

B (23:38)

I got another question switching gears on the entrepreneurial side because I'm thinking about this too. I've been studying sales and enterprise B2B sales specifically. So the question for you is when is a good time to maybe hire your first sales rep and what are some things that you would recommend as far as kind of choosing the talent, testing them to make sure they're a good fit. Any, any thoughts on that? As far as just picking sales talent and the timing of when you should. Is there a certain revenue number that you should aim for to kind of hire like a full time sales rep versus a part time sales rep? Any thoughts on that?

A (24:19)

It's a great question and I am smiling because I spent the vast majority of my life doing enterprise sales myself and then building up a salesforce. So I have many thoughts on that. And it's funny because when I stepped down as CEO of Topia, I was like wow, I never to do enterprise sales again. You know, like begging at the end of the quarter some large company to sign a contract. And then when I started my campaign I didn't really realize how similar the dynamics were except you're just begging an individual to you know, make their contribution by the end of the quarter. And then I just realized, oh, you're going to be doing this for your whole life domains. But so when you start a company, you know, the found I believe the foundation founder should be doing the majority of sales in the early years, principally up to about a million dollars of ARR annual recurring revenue that Varies a little bit depending on the profile of the founder. Right. If the founder is the CTO and very technically oriented, there may be a co founder who's doing the go to market side or there may be, you know, a VP of sales or a senior level person that's been an early hire that can drive the go to market side while the founder is building the product. But for the most part, the founder needs to be involved and be the chief salesperson for the beginning phase. I would say that's up to a million ARR, give or take. And up to a seed round. Yeah, it's critical to know the market. You get really important feedback in the early days that goes back into the product. You can then credibly go to investors and say, I have product market fit, I've been doing the sales, here's what I've heard, here's how I've iterated, here's where we are and therefore fund my seed round. So that's kind of my viewpoint on that. The other side of this is then you start to hire account executives or VP or director or whatever it is that you decide to hire first into some extension. And I think that depends on what else the founder needs to do. You know, how senior that hire is, how involved the founder is going to stay, what their skill sets are. Whether you sort of hire account executives first to get to two or three of them before then hiring a vp, or you hire the VP and say go hire all of the account executives. I hired two account executives first, fairly junior, and then hired a VP and said, okay, go own this. Because there is a point where you, you know, you should be doing the inter an interview, but there is a point where you can't be building a sales organization.

B (27:06)

Yeah. Is LinkedIn a good place to kind of find talent, just put, create a job posting?

A (27:11)

Yeah, I think LinkedIn's a good place. I mean, I would also just be again, conscious of the competition in the market. I'm not. You know, it's always hard to hire recruiters because it's big cost early on, et cetera. But enterprise sales works, enterprise sales productivity models work such that any day that you delay your hiring massively impacts your revenue model. So I think balancing the cost that you would pay a recruiter versus the hours you would spend on LinkedIn and the risk of being off of your revenue plan from a productivity model is an important conversation. Yeah, so that's one thing I think in terms of profile early on, the most important thing is that the salespeople you hire will do lead generation and pipeline building as well as sales and are motivated by that and are motivated by a very big territory. There are salespeople that expect to, and I would say the majority of them expect to start with a pipeline, expect to have a sales development rep or some kind of inbound marketing handing them leads and expect to have a defined territory that is one type of salesperson. That type of salesperson does not succeed in an early stage business. You need people who will hustle. You need people that are excited by having a blank canvas and like literally building things in salesforce as they go building their own pipeline, cold calling and are humble enough to do the work of that an SDR may be doing in a later stage business and be a part of sort of building that up and nimble enough to sort of grow through the company. There are salespeople that are really good in the early days that don't like that earlier, that later stage because they like territories and blank canvases and you know, get excited by the demand gen. There are salespeople that hate the early days and like later, and then there are those that can go through the whole journey and sort of be nimble through the phases of the business. So that I think that is the most important thing to diligence in the early interviewing. I can't tell you the number of salespeople I hired who like early on, who could not do the lead gen side, hated it, hated not having a pipeline, like hated cold calling. And they were just, they were good salespeople, but they were just more appropriate for a stage where there was more pipeline, more infrastructure.

B (29:43)

Yeah. I mean there's the closer and then there's the pipeline. Right. So when you have somebody that's doing the, that can do both. Right. I mean, my judgment, and this is me being new to sales, but my judgment is maybe the people that are more junior, they're not as good sales reps and they're not closers. But what you're saying is if you find the right person, there could be people. If you motivate them and they love your mission, they could actually do both. Right. But does that take away from their time of closing? Right. Because you want to have essentially you want to have like 10 meetings a day and just, you know, out of those 10, you know, maybe close two or three of them right away from their pipeline. Or do you, you know, what's kind of the split? Should they budget maybe a couple hours a week to build a pipeline or is it like half of the week like that, it takes time to do that or you know, what have you seen as far as kind of the breakout when you have those roles that do, you know, kind of the full stack and then do you still. Does that save some money on marketing as well or do you still need marketing to complement that?

A (30:49)

So I think it depends on the stage of the business and the type of business. Whether you're doing more mid market SME type sales, which is higher velocity, lower deal sizes, or you're doing true enterprise, you know, $200,000 ASP plus, longer sales cycles, more stakeholder management, more nurturing. I personally ascribe to the business to the philosophy that every account executive up till you know the business is like 50, 60 million ARR should be doing a portion of their time in lead generation. I do not believe in salespeople that sit back and wait for things to come to them and only close. There are people who do believe in that. It's a little bit more of an old school viewpoint. I believe in people with heart, with hustle, that are builders, especially in a startup. And I think that culture is really important. Those percentages shift through the years. So you know, your first account executive could potentially be spending for the first six months greater than 50% of their time, 50, 70% of their time building a pipeline, doing demand generation, et cetera, because that's what's required when you walk in with no pipeline. But I think in a steady state, we always said they should be spending 30% of their time doing pipeline generation and 70% of their time later on in the cycle nurturing and closing the other model as you get larger. And it's important to build this early on is you do need to build concurrent to hiring account executives who can do demand generation and or lead generation in addition to the actual sales cycle is you need to start hiring some sales development reps. These are people out of college typically who are hitting the phone, scheduling meetings. In certain businesses they should be able to get through the demo phase. In certain businesses they'll grow to be able to sell deals under $100,000. That was sort of our barometer. Also are sort of the, you know, the career path is to get to that, but as you build that up, you know, eventually you'll pair an account executive with one or two SDRs who are feeding them leads in addition to the own demand generation that they are doing. But at Etopia, when I was CEO, we never accepted that a account executive, regardless of how senior he or she was, was just Going to sit there and wait for the SDR to give them leads. They each had a map of target accounts. The SDRs were a little bit easier to navigate, but the account executive would have still have a list of like 20, 30 target accounts. I mean, these would be the largest businesses on the planet and they would need to figure out how to penetrate them, but they would still be doing that.

B (33:49)

And walk me through, if you can, if you're allowed to, maybe your interview process. So, you know, is it like Jordan Belfort, where it's like, hey, sell me this pen, or is it, you know, what, what do you expect them to do when you're trying to hire talent? Do they. Do they do kind of a practice pitch? Is it like a, like a paper that they write or something like that? But I guess, what are some ways that you can identify that talent and just evaluate if they're a good hire or not?

A (34:18)

Well, first of all, there's multiple interviews. So I think there's different screening or qualifying questions at different stages in the interview process. So, but I think thematically the sort of three stages are, you know, does this person have the sort of skills and experience that this role requires? That's like basic level. What have they done in the past? How do they think about selling? How do they approach pipeline building? How do they approach pipeline management? How do they approach navigating, if it's an enterprise business, navigating an enterprise account and doing stakeholder management? What sales processes have they used in the past? How do they approach qualifying leads or not? You know, is there a methodology they use like Medpic or one of those sales methodology? So that's just sort of like, you know, what level of salesperson are they? And a lot of that can be taught, but just trying to get a sense of sort of level and where they are on that journey. Then I think the second phase is what can't be taught, which is the heart and the hustle. Those are more behavioral or sort of values type questions. I always liked the question of what's the hardest thing you've ever done and why? Because sales is hard. A lot of it really sucks. There's just no other way to say it, especially in the early days. You're calling people that disproportionately say no. I mean, fundraising is the same, right? You're calling people that disproportionately say no to you. Some of them do that in nice ways. Some of them do that in not a very nice way. You're pounding the pavement metaphorically. On and on and on. Even when you might be working a big deal and excited about it, you get to the end and someone says no. So and then you eventually get, you know, a great deal on the door. This is not for the faint of heart. And you need to test for grit and tenacity and, you know, how are they going to handle it when the 99th person says in a really rude way, no, are they going to say, and how do they manage that as a person? You know, one of the frameworks that I often use, which I actually read years ago in a Daniel Pink book about a, he was like a vacuum salesman that he had profiled in the book that is this ratio of three good for one bad. So, you know, there. And these are not like big things, but, you know, you're talking to someone that says no to you. Like say, give someone a compliment in the office, hold the door open for someone. Like, send your mother a nice text message message. You know, three things for every one difficult conversation that has like a human keep you up and happy. And so just, you know, getting a sense of how they navigate difficult situations and their values is the second phase. And then the third is, and you know, by that point they should know about the business. We always have people make a presentation and do a mock sales meeting. And with that you can test a few things. You can test presentation skills and communication skills. You can test how much they care, like how much effort they put into the presentation. But you also can test how much they've listened through the course of what at that point will be many interviews about what the business does and whether they can articulate that back to you.

B (37:47)

Sure. And I mean, obviously if they got the job, you know, they're, you know, I always think, you know, being the best candidate in an interview process is a sale too. So I mean, just that whole package of delivery. Right. I mean, the, the follow up, you can even observe the follow up when they follow up about the opportunity. Right. How they package that messaging, all that stuff too. So that's all really helpful feedback. I liked your comment about just offsetting the negativity with a couple, you know, positive statements as well. So it was really helpful. And then, you know, I'd say the final thing with sales is really just communication and nurturing. Right. So with nurturing, what are some tools that you think people should have in their back pocket? Is it, is it blogs as well? Like, should they share some literature or is it really just kind of a follow up and what, you know, it's probably a balance, I'm assuming with being too aggressive versus just slowly checking in. Right. You don't want to check in with them like three times in the same week, but maybe like maybe once a week or something like that. I'm not sure. For like B2B sales, are there any cadences or patterns that you've seen for nurturing and follow up?

A (38:59)

Well, this is where marketing and sales need to work closely together. So you know, it's a very difficult and somewhat unfair situation for a salesperson to be in where they all the only thing they have to say, say all the time in the cycle is hey, just checking in, what are the next steps? Or you know, have you reviewed yet? That is not going to be successful. So this is where depending on the stage of the business, the founder and the marketing department need to be creating collateral materials, events updates that the salesperson can then share through to the prospect, inviting them to webinars that the company may be hosting, sharing news, press releases of funding rounds, press releases of product launches, sharing updates on new products that have shipped and in the case of a SaaS platform that are going to be pushed live, but just giving the prospect a heads up or sharing the release notes that might be published from a public viewing perspective, sharing white papers or blog posts within the business even though the salesperson isn't going to be writing any of that stuff. So you need someone early on in marketing that can be producing content to surround the early salespeople. This is, you know, my recommendation is to hire a sort of a marketing manager level person that is a jack of all trades. We have this exceptional one named Sean at Topia. I think he's been still there who was just integral to growing our US business and could write blog posts, write product notes, write white papers, write a lot of different things, and work very closely with the account executives. That's really what you need. And then you grow the marketing department in tandem with the business growth going forward.

B (40:56)

Yeah, no, it's a good point because I mean, I think there's, there's a couple different flavors of marketing, right? There's product marketing, there's brand marketing, and then the content marketing is a big piece. So I think to your point, you know, having somebody that can kind of do a lot of those things in the beginning and be scrappy is helpful. And then did you guys ever hire like a brand marketing person? Because I feel like that's probably more for a mature business where they really want to rethink the strategy if they want to Do a rebrand if they want to really rethink the logo. What are your thoughts on how that falls into kind of the marketing stack?

A (41:31)

Yeah, I mean, it's an important aspect of it and it depends on to some extent who the founder is and the different stages of the business when you might want to hire that. But I think the important fundamental thing is that a brand marketer is very different from a demand generation marketer. You know, I personally believe that marketing should be oriented towards revenue in the early days and that there should be. The marketing people that are hired in the early days should be very closely aligned with sales to drive pipeline generation. Remember, you need really a minimum of 3x pipeline coverage to hit your number. Like that's a lot. You're not going to get there with just SDRs, just some account executives with hustle and heart who are doing their own pipeline generation or just marketing doing demand generation, all those things. And the magic of the early business is getting that machine working. That's what any series A investor is going to look for is like, where are you on that journey? And then any series B investor is going to look for, okay, do the economics of that work? Do the economics of the interplay between demand generation, the cost of sales and the size of those sales and the term of those contracts, do they work? Does the cost of acquisition and the long term value work? And if that machine works, then you just put more money into it and it scales that I think. And that is not an easy or short process getting that machine working, tying the milestones to the fundraising is a big process. Right. So my belief is that the important thing is to focus on that in the early days. And then once you get the machine working, then you can say, okay, let's rebrand or let's focus on the branding aspect. That's not to say that you can have like really immature branding or bad materials. So you know, you need someone that can do that. But corporate marketing or corporate branding I think can come a little bit later. There are some caveats that to this business, but I think that thematically that's generally the way to look at it.

B (43:49)

And then when it comes to growth marketing, is that also a function that the jack of all trades would manage to like the paid acquisition as well, or do you think that should be a dedicated resource?

A (44:00)

So when I say growth or demand generation, that's what I mean. I think you're calling it growth marketing, I just call it demand generation.

B (44:10)

Demand generation, yeah.

A (44:11)

Right. There's different aspects to that, right? I mean I think the first hire should be able to do sort of a jack of all trades, growth marketer, demand generation marketer, you can call it.

B (44:24)

Whatever you want and then content also along with that as well.

A (44:27)

But that person should be able to create content to understand salesforce and work with the sales leadership or the home founder, whomever's doing it at that point to sort of drive some of the pipeline metrics, et cetera. Demand generation is a particular skill. It tends to be very quantitative, it tends to be very systems driven. Today you eventually are going to need to hire someone who's familiar with HubSpot or marketo or whomever you're using, set up all of those systems, can look at the metrics and really get the machine going again in the terms of the true pipeline generation demand generation machine. And there is going to then be a content focused marketer that works with that person to create the materials to put into that machine. But you got to get to that point in the early days. The jack of all trades marketer should be able to touch on all of those things. Right? Well get you know, basically up to speed with HubSpot or mailchimp or constant contact or whatever you're using in the early days, sort of understand or be have the capability to understand the metric side of the business. But eventually those two things are going to split so that you can get a really sophisticated and proper demand generation machine going.

B (45:54)

That's great. Well, thank you so much. I know we're at time here. Look, this was amazing. I think just your insights into sales and tying that into fundraising as emerging managers or people on fundu is really helpful. So thanks for all that wisdom and all your insights on entrepreneurship and being a fund manager. I always ask this at the end. I always ask for just a piece of life advice that you've carried with you that you'd like to share with us. So anything that you then you have kind of looking back, it could be a quote, it could be just a piece of advice from a mentor would love that. And then if anybody has any final questions, I'll shout those out as well. But anything that you'd like to leave us with would be great.

A (46:38)

Oh gosh, he threw that at me. Let me think about that one thing that a coach in the past or a facilitator in the past said and then a another CEO who happens to be a female CEO of one of the largest energy public companies in America. She's incredible. Also encouraged me to see is the notion that all people and circumstances are your allies. I think we can, in fundraising or in any sort of business, sometimes come at things with a defensive posture, sometimes take feedback or take no's, or take whatever it is negatively. But to be able to just reframe that and say, okay, what can I learn from this? And this person is not out to get me in a personal context, but this person is giving me a gift that I can learn from and that I can use to further my goals is a really important principle that's really helpful.

B (47:48)

And I think that, I mean, I think part of sales too, you know, which was probably implied, is just having a positive attitude. So I think this also piggybacks off of the other, the nugget that you gave us earlier. Right. If you get, you know, a no, you know, try to do three nice things. So I think that positivity, especially in sales and fundraising is super important. So.

A (48:12)

And that one really, really, really works. Like it's, you know, if you're feeling super down, just like pick up the phone and call an old friend and just say, hey, I was just thinking about you and I, you know, wanted to tell you, you know, there's something about like we receive positivity back from people as humans. It really reframes your perspective.

B (48:30)

Yeah.

A (48:30)

Or even just like, you know, when you're going to lunch or pick up your smoothie, like say thank you so much, I hope you have a nice day. You know, to the person at the catch register, like most people don't say that. They just like grab their smoothie and tap their card and run and really appreciative of that.

B (48:46)

Sure, that's really helpful. So we got one question. Do you have like maybe 30 seconds for a really quick one? So Daiji just wants any tips on incentivizing pipeline generators or deal generators. So I guess, you know, obviously commission. Any tips on just kind of the commission split or just compensation to keep them still hungry and excited? And one tip that I will say, I mean, I learned this in a video that I watched recently. Some people say to hire two sales reps at the same time so that there's always kind of a competitive spirit. But anything else that you have any nuggets on, you know, your years looking back at building a sales team to incentivize them.

A (49:29)

So I think it depends on what you're talking about. I mean, for SDRs, they should typically be paid on meetings booked. And then for account executives, they should be paid on revenue generated. And for demand generation people, they should have a pipeline marketing Contributed pipeline target that they're paid on. I am not a fan, you may hear different views from other people, but I am not a fan of having like a very complex set of metrics like account executive. This much pipeline generation, this much at this stage, this much business close. The reality is they're not closing business if they're not generating a pipeline. So that is, for me, I just keep the targets super simple. Like what are we trying to get to? I don't really care how you close business. Maybe you don't need 3x pipeline coverage. You probably do, especially when you get to scale. But in the early days you may not when there's no one else in the market. So I don't really care how you get there. Just close the business, hit the number and then if they exceed the number, then having really, really aggressive accelerators, you know, I learned sale, the sales methodology of, you know, really, really paying people for performance. Like outsized accelerators. It can be expensive for the business, but if you have salespeople in your business making a million dollars a year off of a 200k base salary, like everyone wants to work at your business, that person's going and telling all his buddies or her friends like that they're doing really well. It goes through having very, very aggressive accelerators and it does pay dividends.

B (51:10)

So when you say accelerators just be generous with their commission payouts, is that what you're saying?

A (51:14)

Yeah. I mean, in the enterprise side, the typical structure is 150% of the comp is base and 50% is variable tied to hitting their targets, their quotas. Once they hit the quota and start exceeding it, then having a pretty exponential increase in the comp that they can make past that tied to stages at which they accelerate it.

B (51:42)

And to your point. Yeah, and I mean, that's important too, because to your point, I mean, in the big cities like New York and San Francisco, there's another great company right across the street that'll pay them like 20 grand more. So, you know, being generous will kind of keep them there. And it's going to be more expensive for you to have to hire a new person to go through the whole process again, Right?

A (52:00)

Yeah. I mean, most people are going to negotiate for higher comp, right?

B (52:05)

Yeah.

A (52:05)

And then expect 100, another 50% of that in variable, and then somewhat take the accelerators with a grain of salt. I mean, this will be different in a later stage business, but in the early days when there's no proof points, you know, that's in my experience how most people evaluate sort of offers where, you know, I believe you want to get to as an entrepreneur is or CEO is a board member is the lowest. And I don't say this from like a negative perspective because people should be paid fairly, but the most reasonable base salary with a very, very aggressive outperformance plan.

B (52:45)

Sure. That was really helpful. Well, hey Bryn, thanks so much for being generous with your time and really good spending time with you. And I hope you have a great week and hope to catch up soon in person at some point.

A (52:56)

Thank you so much. You have a very good day, Joel. And thank you so much for having me on.

B (53:01)

Thank you.

A (53:03)

Anyone wants to follow up, you can follow me on Twitter rynspeak, connect to me on LinkedIn Bryn Kennedy or reach me on bryn kennedymail.com Great.

B (53:14)

Have a good one.