The Journey from Operator to Advisor with Forethought's Jeff Ignacio

Sean Lane: Hey everyone. Welcome to operations, the show where we look under the hood of companies in hyper growth. My name is Sean Lane. So I have this uncle, his name is Ron, and Ron's the type of person you turn to for career advice. He told me once very early in my professional career that there are three phases to any job, learning, doing, and teaching, and only when you're doing all three at the same time have you completely mastered that job. I couldn't help but think of my uncle when I spoke with our guests today, Jeff Ignacio. Jeff is the head of marketing and sales operations at Forethought, an AI support platform, but on today's episode we're not actually talking about Jeff day job. We're going deep on something else, advising. And we're going to talk about how Jeff has leveraged his operations experience at companies like Google, PatientPop, AWS, and UpKeep to build an impressive list of advising engagements. Jeff is someone who is learning, doing, and teaching all at the same time inside of hyper growth companies. In our conversation we talk about the content flywheel he built that led to his advising opportunities, we cover the three types of advisory work that he typically sees, and Jeff will tell you exactly what to ask for in exchange for your next advising engagement. To start though, I wanted to go back in time to figure out how Jeff realized that advising was even a potential opportunity in the first place, and it turns out it had a lot to do with lessons he learned about building his personal brand.

Jeff Ignacio: So back in 2019, 2020, I was working at a company called PatientPop, and our SVP of sales was a gentleman named Justin Welsh, and then our VP of inside sales was a gentleman named Kevin Dorsey. People who are listening to this may be familiar with those two names because they have massive followings on LinkedIn, and you get much larger followings especially if you are talking about sales. You don't get as high of following if you're talking about revenue or go to market operations. It's just not that big of a market. But they were doing this thing called building a personal brand on LinkedIn, and so they were posting every day, and I mocked and joked to them that they were looking for new jobs by posting so much, and it blew my mind. They were like, " Look, we're building a personal brand, we're empowering the people who work with us to also build their own platform, because sellers and marketers and CSMs, whatever your role is, you can be a brand unto yourself, and it's just an additive to the business itself." So I took their advice, started posting on LinkedIn and just sharing my thoughts really. There was no goal to work towards. It was just for fun. And so the pandemic hit, everyone worked from home, and for some reason LinkedIn just had a ton of engagement during that time, same with all the different Slack communities. And so at first it wasn't advisory gigs, it was just invitations to join a podcast like we're doing here, or going to a webinar and lending my expertise, but sooner or later there were some companies who were looking for folks who had a personal brand to advise them on a couple of things, and so many of these requests just started coming inbound. At first I had no idea what to make of them, so I just took every single call that came my way, but sooner or later I found an idea where I could be helpful. So there are some advisory gigs that come my way that quite frankly aren't a good fit, so I'll politely decline, but the ones that are a good match, at least for what I can provide to them, we'll talk about it and see if my bandwidth can allow for it. So that's how the advisory gig started coming in, it started coming inbound, and off of the personal brand, so hopefully this is a plug for someone out there to build up their expertise personally, your personal brand is your reputation at the place that you work first and foremost, but if you have the bandwidth and you feel like sharing with others, you can do so through LinkedIn, through communities, through other avenues.

Sean Lane: So I want to come back to how you've been parsing some of those opportunities in a minute, but to follow up on your last point there, this may seem simple to you because you've been in the habit of it for so long, but you're sitting there, you just make this decision to invest in your personal brand, to share this stuff out, what do you talk about? What are those first handful of things where you're like, " Okay, this is worth sharing, this isn't worth sharing. I don't know whether this is good or not, but the engagement's going to tell me." How did you think about that?

Jeff Ignacio: I wish there was more of a design to it, but quite frankly it's when you're in revenue operations, or if you're in a siloed role like sales or marketing operations, you get to see how the business works, and typically you'll actually see your own personal business, but believe it or not, the problems you're solving for exist at other companies, and so sometimes it would be helpful to just think through first principles, maybe describe the problem, not necessarily revealing what's happening at your company, but just in general. If you were in a situation where you were solving lead routing and you were in a world where you had PQLs on top of your MQL structure and you've set up these different things that are happen happening to your company, believe it or not, when you go into the community and you share that story with someone, someone else is going to raise their hand and say, " Yeah, I'm going through the same thing. Here is how I've solved it. Or I haven't solved that at all. I want to talk to you." And so when I'm thinking about writing, there's a whole library of things that I put on the shelf, and so I'll come revisit it. I have a Google Keep, which is like Evernote, so I'll just have a random set of dozens of notes and I'll just literally write stories that I'm going through, and I'll revisit it in a couple weeks time and keep expounding on it. And I'll take one of those stories that I really like and I'll post them on LinkedIn or I'll share them in a community, and it gets either really good engagement or really terrible engagement. If I was scientific about it, I would reverse engineer what would be my highest performing post, I would just tweak it slightly, and then repost it, but I like writing original concept from scratch.

Sean Lane: Jeff makes this all sound so effortless, but he's giving each of us a blueprint to follow if we want to build a personal brand like the one he successfully crafted for himself. And honestly crafted is probably too deliberate a word. As Jeff said, he started by simply talking to communities about the problems he himself was working on. People will relate to that, and then you can build up both your expertise and your brand at the same time. For Jeff, over time, those posts started to evolve into a full blown content flywheel. Here's how.

Jeff Ignacio: There's a content strategy that I like to employ. So when you write something, there's implied scale to it. So I'll give you an example. If you're writing a series of post, what's to stop you from collating it and creating a greater piece of content that could become an article? And if you're writing multiple articles, what prevents you from turning that into a course? And then when you create a course, what prevents you from turning that into a book? And so there's a flywheel effect, and that scale that I talked about is going from small content to large content. You can also do the same thing going from large to small. For example, when you're doing content marketing, when we're done with this podcast, there are hopefully going to be some sound bites that you can snip it, put those out there on a number of different social channels, that's Twitter, that's Instagram, LinkedIn, whatever it's going to be, there are going to be varying levels of engagement because the audiences in those platforms are going to be somewhat different. But to me I believe that when I'm writing these pieces of content, they're not just there for my practice and what I bring every day to my professional role, but these other sides of income that I've created for myself, there's a flywheel effect to it.

Sean Lane: First of all, I love that cascade of article, course, book, and vice versa, but I also think that there is something to the fact that you've been in this give, give, give mode and then all of a sudden, not all of a sudden, these opportunities started making their way to you. People are like, " Wait a second, I could be an advisor." But this has been, to your point, years of you putting this content out, codifying it, refining it, and so you mentioned that they started to come inbound to you. What happens next? How do you think about either evaluating those opportunities or meeting with the companies that are reaching out? Because, to your point, there might be different flavors of engagements that either they're looking for or that you want to provide.

Jeff Ignacio: As an advisor, what you're investing is not capital just like a venture fund. If I was in VC, I would be investing some of my LPs money. Maybe I'm thesis driven, maybe I'm looking for certain industries that I want to be a part of, but I'm not lending that. What I'm bringing in is my intellectual capital, my experience to the table, and so the advisory roles have varying different capacities or requests that they're looking for. For example, some folks are looking to piggy back off your personal brand. In those instances, well, okay, if you want to use me as a marketing piece, I'd hope that our values align and that I'm not tying reputational risk to this venture. The second piece, which I think is more interesting, is product direction, so I'm targeting certain personas, you may have some insight to that persona. I've noticed an uptick in number of entrepreneurs building solutions towards the revenue operator. We don't represent a very large percentage of seats at the company, but I can tell you we do have an outsize leverage impact at companies. And so when folks are engaging me, they're saying, and they always say this, " I would love to pick your brain." It's like this pick your brain phrase that comes out all the time. I would love to talk to you about product direction. And that makes perfect sense, particularly in a world where you have pre- product market fit and you're trying to test out some of your hypotheses and you're developing a product direction, those are fun. I love doing those as well. The third option of advisory that comes to me is we want to know more about your persona, what does a revenue operations leader or operations individual contributor care about? What are some of the common problems that they're going through today? And what are their solutions? And could this thing that I'm building be a replacement for that solution? And would you be willing to pay for it? And I think there's an entrepreneurial element there that is hugely exciting for anyone that has an opportunity to advise startup or maybe even a later stage company, and that's something that you get to do outside of your own workplace.

Sean Lane: There are three main types of advising engagements that Jeff spends his time on. One, companies looking to leverage his personal brand, two, companies looking for feedback on their product direction, and three, companies looking to better understand the RevOps persona. And again, these are largely inbound opportunities coming to him as a result of that flywheel that he was talking about, posts that turn into articles, that transform into courses, and then ultimately become books. That's a lot of content proving Jeff's expertise to the market. He's not hiding behind pithy one- liners or surface level insights on LinkedIn. His content is rich, tactical and helpful. With all that being said, as we called out at the top of the show, Jeff also has a day job too. So how does he manage to balance this advisory work and the supporting content efforts with his role at Forethought?

Jeff Ignacio: So these advisory gigs, they're like a monthly board meeting. So companies will come to you, engage with you for a limited amount of time, so 30 minutes to an hour every other week or every four weeks. At first it might be heavier than that because they're going through their own discovery, they're learning, but as they get more comfortable, I actually think the role of an early advisor like myself starts to wane, and the type of advisory that they might need would shift more towards the day to day outcomes of the business itself. So in those capacities, if they were willing to engage with me and I did have enough bandwidth to focus on them, then I would engage with it. But overall I would say in terms of income streams I do a little bit of side consulting for some legacy clients that I've worked with just for years, I continue to maintain the lights for them after hours, I do have my day roll, so anything outside of that has to be very few and far between. So I will advise probably four hours a month, which isn't too much of a tax load.

Sean Lane: Got it. And so we've talked a lot about these different themes of what might be in it for the companies, what's in it for you, what do you get out of these advisory engagements?

Jeff Ignacio: So if there are any entrepreneurs listening out there, these advisory gigs, they're mostly equity based advisory agreements. So you're on the hook for a two to three year cliff, a quarter or a monthly vesting schedule, depending on how you design it. Sometimes there are milestones in your agreement that you'll agree to, but I do think it makes sense to put in terms what the nature of the advisory agreement would be. There are other opportunities where there are more cash compensation, those are less interesting to me because then it would feel like consulting. I'm more interested in tying your outcomes to my advice. And if my advice is doing well, the equity would be worth something in the long run.

Sean Lane: And came into this, like you said, relatively new in the last few years. And so if there's somebody listening right now and they're hearing, okay, I can build my brand, I can start to seek out potential opportunities like this, but then they get to that moment where they actually have to have this equity conversation with a first time founder who's trying to find an advisor. Where do you even start? How did you figure out, okay, what's the right amount of equity? What do I think is worth my time and effort? How did you think about that, or who did you learn from to position yourself to be able to have those types of conversations?

Jeff Ignacio: I heard this once on a podcast, I think it was with Jason Calacanis or David Sacks, I can't remember, they were mentioning that these advisory agreements tend to equate to, let's say, it's 500 to $1,000 an hour and you're advising 12 hours a year. It's a small amount of money, 12, $ 24,000 worth of equity at whatever the par value is at the time. And if you extrapolate that at a early stage company, the shares are typically like pennies, but you get to series B, series C, series D, they could be easily worth a couple dollars, so you easily 10X, 20X whatever the grant is going to be. So it might be small potatoes at first, but if the business ever does have an exit, or you have an opportunity to do secondary, there are fantastic valuation multiples on whatever that grant is going to be. But just try to baseline it as a normal consulting arrangement. That's how I would say it, and say, " Instead of compensating me in cash, how would an equity agreement work out?" And then you have to obviously work out what the par value per share is and validate that, but that's always a conversation to have with the firm.

Sean Lane: Take Jeff's math with you if you're starting to think about these advising relationships for yourself, multiply an hourly rate by the number of hours per year that you intend to spend on that advisory and calculate what that dollar value would be worth in terms of shares in the company instead. It's so helpful to have someone who's already gone through this a number of times to show the rest of us the way. As Jeff goes through these engagements, it's clear that he's spent time thinking about the role he wants to play and the niche he's carved out for himself in the market. So what does he hope comes of this whole thing? When he looks back, what does he hope to have contributed?

Jeff Ignacio: So if I look at back at this time, these companies I'm advising, I hope they make it, because these are entrepreneurs who've come to me. I hope that their success is somewhat reflected from some of the advice that I've given them at that particular stage. That would be amazing. And then secondly, it's great to help others out. A lot of these did come inbound. I wasn't expecting them. We talked about their vision, where they wanted to go, and I was hugely excited about some of these opportunities. And so this is a real privilege and a real honor. So if they do succeed in one form or another, they go public, they become a large private company, or they get acquired with a great firm that has super synergy around their capabilities, I would be really proud of that. Me personally, where I'd like to go, I don't think anyone wants to be in their role forever. You want to pass the torch onto others so you can have the opportunity to build a succession plan and do something else. I do see more revenue operators becoming COOs at firms these days. The same level of running the rhythm of the business, bringing in capabilities, building the infrastructure, holding accountability standards and raising them each year, those are traits that COOs bring in across not just the go- to market functions, but across the business as well. So I do see myself taking on some of those C level roles in hopefully the medium term future.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months.

Jeff Ignacio: I really liked Amp It Up by Frank Slootman, former CEO of ServiceNow and Snowflake. He talks about a lot of things there that I really enjoyed.

Sean Lane: Cool. I just started it so I will report back.

Jeff Ignacio: Sweet.

Sean Lane: Favorite part about working in ops?

Jeff Ignacio: The most difficult part that I do enjoy is aligning different points of view and rallying them towards a North Star.

Sean Lane: Flip side, least favorite part about working in ops.

Jeff Ignacio: The same thing, dealing with multiple personalities and also getting to the North Star. The journey is difficult, but once you get there, it's amazing.

Sean Lane: Weird, I've never heard that before. That's very strange. All right. Someone who impacted you getting to the job you have today?

Jeff Ignacio: Susan McGovern, she's an SVP of RevOps, at Legion Technologies. She made the first bold move of bringing me on as a, quote unquote, director of sales operations at a company called Visier. I was a director in title alone, I did not manage any individual, but she gave me the opportunity to do sales operations, a bonafide sales ops role. And before that I was in FP& A.

Sean Lane: Awesome. Well, shout out Susan. All right, last one. One piece of advice for people who want to have your job someday.

Jeff Ignacio: Be curious, be empathetic, and be relentless.

Sean Lane: Thanks so much to Jeff for joining us on this week's episode of Operations. Special shout out to Megan Murphy for helping to make the introduction. Thank you, Meg. And of course, thanks to Uncle Ron for providing the inspiration for the top of the show. If you like what you heard, please make sure you're subscribed to our show so you get a new show in your feed every other Friday. Also, if you learned something from Jeff today or from any of our episodes, make sure you leave us a review on Apple Podcasts or wherever you get your podcast, six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.