Building Trust in Product Leadership with The Product Coach Tami Reiss

Randy Wootton

00:00:04.880 – 00:00:50.532

Hello, everybody.

This is Randy Wootton, CEO of Maxio and your host of SaaS Expert Voices, where we bring the experts to you to talk about what’s going on in SAS or how you could be more successful in SaaS. With me, I’m delighted to have Tami Reiss, who’s a longtime product expert, but she’s also been CEO and president.

She has 20 years of experience helping startups, established enterprise companies, and community organizations define their product strategy and set up product organizations for scale. Just that. We’re going to dig in on that.

Most recently, over the last four years, she’s been the founder of the product leader Coach, where she focuses on coaching product leaders speaking around the world about management and strategy. And she has a book in the work for children called what do product managers do? Welcome, Tami.

Tami Reiss

00:00:50.716 – 00:00:52.140

Thank you so much for having me, Randy.

Randy Wootton

00:00:52.180 – 00:01:02.390

It is absolutely my pleasure. And let’s take that last part. What do product managers do? What inspired you to write that book and who’s it targeted to and how’s it going to help?

Tami Reiss

00:01:02.930 – 00:01:13.554

All right, so we’ll go with the target and then go with inspiration. So what do product managers do? Is a children’s book, meaning that there’s children’s illustrations and the entire thing rhymes.

Randy Wootton

00:01:13.722 – 00:01:15.170

Wow, that’s ambitious.

Tami Reiss

00:01:15.330 – 00:01:25.310

The entire thing rhymes. And the subtitle is a primer for aspiring PM’s of all ages and parents who aren’t sure it’s a real job.

Randy Wootton

00:01:25.470 – 00:01:44.502

That is hilarious. I remember coming out of business school, this was 2000 and I was coming out of the military. I didn’t have any skills.

You know, I know just a little bit about finance, a little bit of accounting. The first job I landed was product management. And we didn’t have any courses about product management in business school.

I was like, I had no idea what to do yet.

Tami Reiss

00:01:44.526 – 00:01:45.342

You got hired, right?

Randy Wootton

00:01:45.366 – 00:02:12.360

And I got hired. I think it’s one of those.

You got hired because he seems like a smart guy and he’s a, you know, clearly can get stuff done, so let’s just drop them in. And at the point we didn’t have a product management discipline at the company I joined. It was one of these new startups.

So I found this thing called pragmatic marketing, which it sounds like you had gone to as well. I went in 2000. 2001. But you want to talk a little bit about your own journey to product management and why ultimately that led to writing this book.

Tami Reiss

00:02:12.820 – 00:03:21.862

Sure. So my first job out of grad school, out of business school was actually a fundraiser. I was a fundraiser event planner. It turned out.

I was the fundraiser event planner who cared about which zip codes worked best and was a b testing call scripts. But I didn’t know those words. That was just my natural inclination. And I went to the UCLA career center, of all places, because I’m a Bruin.

And they had a website and they were helping me find a new role. And Farmers Insurance had an associate product manager role on, and it was math and it was creativity and it was marketing.

And I said, okay, sure, I can do this. And I got the job, and I was paid less than men, but we fixed that. Legitimate story. Wow.

But one of the things that happened there was the product development team, which is what we now call product management.

Saw what I was doing and they said, Tami, you’re a little too creative to just be product management, which was pretty much filing things for states. We’d like you to be part of the product development team creating the new offerings.

Randy Wootton

00:03:21.926 – 00:03:22.790

We have got it.

Tami Reiss

00:03:22.870 – 00:03:42.134

And so I joined the product development team, and it’s been off to the races since then. But I also went to pragmatic marketing.

They sent me to pragmatic marketing, and I learned about basic product management, which we call product development. And I got to stay for the extra day back in 2008 on Agile.

Randy Wootton

00:03:42.262 – 00:03:45.702

Oh, got it. You got the extra special package.

Tami Reiss

00:03:45.886 – 00:04:06.952

And I was like, this is amazing. This is such a great idea. Why not do quick estimates of things and break things into small pieces? This is incredible.

Not sure why this isn’t the way we’re doing it. And I brought back t shirt sizing to find farmers insurance, and that was not something that they were ready to adopt.

Randy Wootton

00:04:07.016 – 00:04:08.656

Oh, and why was that?

Tami Reiss

00:04:08.808 – 00:04:14.264

Well, we had engineers that were offshore in India working in cobalt and mainframes.

Randy Wootton

00:04:14.312 – 00:04:15.840

And this was 2008.

Tami Reiss

00:04:15.960 – 00:04:21.792

Farmers Insurance was the first company west of the Mississippi to get a mainframe computer.

Randy Wootton

00:04:21.936 – 00:04:22.780

Okay.

Tami Reiss

00:04:23.200 – 00:04:36.026

And like many other companies in the financial services, mainframe was just something they couldn’t get rid of. I’m pretty sure JPMC is still using their mainframe as well, because you don’t delete mainframe, you only add on top.

Randy Wootton

00:04:36.098 – 00:05:19.742

Right, right. Talk about the quintessential monolith. Right. It just goes on and on and on, but. Got it. So they were more waterfall, not agile.

Couldn’t embrace this new methodology, but that launched your career.

Similarly, when I went to pragmatic marketing, I just remember it being this awesome experience, and they had this firm framework, the schematic they shared, and all the different, all the different activities throughout the process.

The other thing that was super valuable for me was the distinction they made between what they would call product or marketing activities versus product management activities and project management activities. And it was like a checklist. As I was working to launch a product, I had all these different things in the sequence that they needed to have.

I’ve used it ever since and it’s been 24 years. I continue to recommend it to people.

Tami Reiss

00:05:19.906 – 00:05:27.038

Honestly, like, they get a bad rap, but because they’re like old school. Right. They’re like the pre Silicon Valley.

Randy Wootton

00:05:27.134 – 00:05:28.086

Right, right.

Tami Reiss

00:05:28.238 – 00:06:05.948

But in reality, the stuff they’re teaching is so core and probably would have been solved.

A lot of the problems that are currently going on with product management where people were so focused on the internal and working with engineers as opposed to working with customers, working on go to market activities, making sure things were meshed. So seeing that Venn diagram, because, I mean, you and I are SaaS people.

Like if you’re a B, two B SaaS product manager and you’re not talking to your sales people, stop what you’re doing right now and go find one. Right?

Like talk to your salespeople, talk to your customer service people and start getting to know what’s going on, because living in a bubble is not helpful.

Randy Wootton

00:06:06.044 – 00:06:09.132

Well, that’s great context. So when does your book come out?

Tami Reiss

00:06:09.316 – 00:07:06.910

So I just launched the MVP.

Actually, I was speaking at the product collective industry conference last week and they have been such a supportive group for me that I created a video of me reading the like Google Slideshow version with the cool illustrations for their community to listen to and give feedback on. But I’m hoping by the end of the year to create an official YouTube video of that. And if there is enough demand, we will put it into print.

But it’s possible it might just end there.

And that’s okay with me because if it gets lots and lots of views on YouTube and it helps parents explain their jobs to their kids because that was the inspiration. I had a daughter and I had no resources to explain what mommy does. And I mean, we’ve gotten great feedback so far from kids, from parents.

Like, the most common thing to be said is, oh my God, this is awesome.

Randy Wootton

00:07:06.990 – 00:07:54.982

That’s great. Well, yeah, please do share with me the link. When it becomes available, I want to share it with my kids and say, hey, this is what I used to do.

And also it’s a viable career option. I think it’s this really interesting career. It’s where I started my career. And then that you get to balance to your point.

You get a little bit of the finance, the modeling, you get the marketing, the creativity, you get the defining process and operations. You get to work with engineering. That’s why I describe myself as being technical but not an engineer.

Translating business requirements, launching things. And I also think it’s a great. As we’ll go to, one of the topics we’ll deep dive in is preparation to be a general manager and then become a CEO.

If you’re running it like a little business. And how are you investing resources? What are the returns? And how do you create features tied to NPV?

Like, there’s all of these things that you learn in business school come together.

Tami Reiss

00:07:55.046 – 00:08:40.184

As a product manager, I incredibly agree with you. I didn’t realize that until I became a CEO. I was brought in to be a CEO of a small consultancy. And originally I said, no, no, I’m a product person.

I want to be CPO. And then within around six weeks, I was like, oh, this is what a CEO does.

Yeah, no, I’m ready for this because I think holistically, I think systemically, and I am okay with iteration. Right.

Like, to be a CEO means you’re going to make decisions with incomplete data, and you have to be confident enough in that to let other people follow you and empower them to do things. The same way product managers empower engineers to do things and then monitor it to make sure it works.

Randy Wootton

00:08:40.232 – 00:08:58.242

That’s right. Absolutely. I think that’s probably one of the key insights of being a CEO, is you’re never going to have all the data that you want.

You’re always going to have too much data. So at the end of the day, you got to make some assumptions, and you’re getting paid to make the decision.

Now, you take input from lots of different people, but if it doesn’t work, they’re all going to point at you and say you screwed it up. So.

Tami Reiss

00:08:58.426 – 00:09:00.150

Sounds like a product manager, though.

Randy Wootton

00:09:00.450 – 00:10:57.660

That’s what I’m saying. That’s a total parallel. Well, great. Okay, well, today’s conversation, we talked about what we can do in the next 30 minutes or so. Three parts.

One was establishing a winning strategy. Number two is why you need a coach as a product leader.

And then we’ll close off the speed round, which is your favorite book, your favorite I metric in your favorite influencers. So with that, when you and I were doing our pre reef, I was introducing you to what then was the seven secrets of success.

I’ve now expanded it to eight secrets of success. Whoa. I know it took a lot of arm wringing on that because I like the alliteration of seven secrets of success.

But I have another story for another time. But within that there’s seven things. One of them is establishing a winning strategy.

This is number two in my book, because number one is you’re ultimately responsible for the results, because if your company is not thriving, you’re falling short and you’re going to get replaced. And the overall resource is around delivering shareholder value in line with their expectations.

And I’m talking about companies that are VC or PE backed, where you’re playing with other people’s money. You’ve come in like what?

My sort of charter these days is coming in as a professional CEO to help move things forward or with Maxio, accelerate the integration. So you got to deliver the results. As part of that, though, you got to establish a winning strategy.

And one of the things I think about is if you’re a new CEO, you come in, one of the things you’re trying to figure out was what was the old strategy? Were there problems with that strategy? Was it not addressing the right challenges?

Was it not set up to articulate where you can win and how you’re going to win? My favorite book is playing to win, which outlines a whole strategic construct.

But it sounds like you, and you’re coaching today at the product leader coach, where you coach both product leaders and CEO’s and other executives. You spend a lot of time looking at this idea of strategy. So sometimes it can feel overwhelming talking about strategy.

But can you talk us through your overarching approach to establishing strategy, the future you want to create your kingdom, and then we’ll just pull it apart a little bit?

Tami Reiss

00:10:57.780 – 00:12:11.428

Sure. So overarching.

My philosophy centers on everything as a product, even you, which means that no matter what it is you’re working on, there are customers that, or that whatever you’re working on fills a job for, and you should be trying to solve their problems. And as you’re going through that process, you should get feedback so you can iterate.

And so that applies to your board deck, that applies to your organizational chart, that applies to you. If you’re applying for a job, that applies to the product you’re putting out into the world, new features for adoption, etcetera.

And so I believe that’s the core of the product mindset and that it can be applied to anything we’re doing. And so the last part of that product mindset is making sure you have a vision of where you want to go.

So once you’ve understood your customers problems and the way you think you’re solving them, you have to set forth a vision, like a storytelling vision, where there’s this group of people that are currently plagued with something.

They have some sort of migraine problem, and we are going to solve that for them, and they are going to love it, and they’re going to love us for providing it to them.

Randy Wootton

00:12:11.524 – 00:12:11.900

Right.

Tami Reiss

00:12:11.980 – 00:12:13.700

And their lives are going to get better.

Randy Wootton

00:12:13.780 – 00:12:28.172

Got it. It’s the before and the after. It’s like this is the problem that is existent in the marketplace, persistent and pervasive. Lots of people have it.

That helps define your. Both your TAM and your SAM. Right. There’s a market opportunity, and it’s a big problem. It’s a big problem, right.

Tami Reiss

00:12:28.196 – 00:12:39.844

Like, it’s something they understand as a problem. They’ve been looking for a solution.

Even if they’re currently using Excel or a piece of paper as their solution, they at some point hit something that says, I need something better.

Randy Wootton

00:12:39.932 – 00:13:05.438

Right. And you’re offering them. You’re painting the picture of the promised land, and that’s why people always use in the market materials.

Here’s why winners choose us, and here’s the things you get and the value prop. And then the next step is helping them understand why you’re the provider that they should choose at that point. Great.

So that’s the creating the vision of the future. You want to create it. Also, as we were chatting earlier, it helps your own company employees better understand.

Tami Reiss

00:13:05.574 – 00:14:05.724

It helps with everything. When you have a company, you have a really strong company vision.

It helps everybody make decisions on their level because especially if the middle management is doing their job, which means connecting the dots from the larger company vision to the activities being done by an individual team, then it doesn’t make a difference.

If you’re a CS person who’s answering tickets, SDR, who’s doing outbound calls, or you are an engineer who’s building infrastructure, you understand the purpose of your job is to do something which supports something else, which supports the larger vision becoming a reality. And that sense of connection helps people make decisions on their level because they say to themselves, okay, is this going to help this or not?

Is this going to be valuable or not? Is this going to be impactful or not? And most importantly, is this the most valuable? Is this the most impactful thing I can be doing at any time?

Randy Wootton

00:14:05.852 – 00:15:20.336

I think you nailed it on a couple of fronts, just kind of repeating what you’re saying is this whole idea of building community and culture is about building connections.

There’s a great guy that I interviewed a couple of weeks ago that has written a book on this, but it’s connections to the purpose, connections to the leadership and connection to the peers. And lots of people talk about engagement, employee engagement.

But I do think, to your point, the vision can sometimes feel Dilbert yes, it shouldn’t be. Yeah. So you just want to make sure there’s alignment. How do you create alignment?

How do you put an operating system in that, a company operating system that helps everybody understand what they’re trying to achieve and they can show the impact they’re making. And to your last point, informed trade offs, because I don’t know what the right trade off is.

I described truth is on the front lines and you need people to tee it up and say, hey, I could either do a or b. Here are the trade offs. Here’s what I would do.

You say, well, that makes a lot of sense, or here are three other things to think about as you’re evaluating those trade offs. But we can’t do it both.

And I think that is often the challenge with younger people, is they feel like they’re overwhelmed, but they don’t have clarity around how to make the decisions of trade offs and be okay with escalating it and say, look, you just told me to do that. That’s different than what you told me to do yesterday. Which one do you want me to do? Help me understand why this is the.

Tami Reiss

00:15:20.368 – 00:15:30.840

Right new direction and it’s management’s responsibility to explain why it’s the right new direction or to say, actually, no, what I said, the first day is still the priority. Second day is what you should do next.

Randy Wootton

00:15:30.880 – 00:15:31.264

That’s right.

Tami Reiss

00:15:31.312 – 00:16:27.588

That’s why they were in that order. But I think that something like there’s this whole discussion of founder mode, manager mode, whatever.

The essence of management is not answering that question for your employee. When they say, which should I do or which of these two things should I do? Me and this other person are disagreeing.

You don’t answer it because that’s micromanagement. They will only come to you with every question.

Instead, you give them the frame of how you would make the decision and you say, well, it’s really important that we’re having impact on this particular thing which is related to our vision. Which of these two things, if you were to have a conversation between the two of you, will elevate us towards that vision?

Which of these two is going to be most factful? Which of these two is going to be most valuable and decided for yourselves?

You don’t need me, but you might need me to remind you how do you frame the trade offs?

Randy Wootton

00:16:27.644 – 00:17:30.809

Yeah, I think that’s a great reminder. Two things pop for me. One is I do think what happens is we’ll get to this in a second. When you describe is define your kingdom.

And so how to narrow this down where you can have a set of objectives that are meaningful to either a function or an individual. And companies use all different types of programs, KPI’s, MBOs, John Doar’s okrs. I don’t care. I use okrs.

And I do think that then if you give them the objective, you leave it up to them to come up with a plan to achieve that objective. Having said that, I do think a manager’s responsibility is to be a thought partner and to help people think about what are their current assumptions?

Like, why are these the options they’re evaluating? Are there three other things that they could be thinking about, not ultimately make the decision?

Or, I mean, sometimes you have to make the decision because they’re making the wrong decision, but if they’re going to make the wrong decision, is this one of these things you can let them go do and have it be hard and then debrief it? And if you create a feedback loop on how that’s going, would you change courses?

I think to your point, you’re helping them develop their skills and capabilities.

Tami Reiss

00:17:31.589 – 00:17:43.141

Yeah.

And what I would add is that in the OKR model, which totally supportive of John Doerr recently actually gave a TED talk about this, that the objective is actually supposed to be inspiration.

Randy Wootton

00:17:43.205 – 00:17:43.809

Right.

Tami Reiss

00:17:44.549 – 00:17:46.877

And too often it’s like, increase revenue.

Randy Wootton

00:17:46.933 – 00:17:48.049

Right? Yeah.

Tami Reiss

00:17:48.349 – 00:18:19.582

And when it’s inspirational, when you do describe it as a vision, when you tell it as a story, it’s easier for people to understand what will be better. Right. When you’re trying to increase revenue, which isn’t gonna have higher impact on increased revenue, that’s more nebulous. Right.

But like, which of these is going to increase our customers satisfaction around using our tool, which will make them like us more and use us more because we are solving more problems, it’s a lot easier.

Randy Wootton

00:18:19.686 – 00:18:48.920

Yeah, you’re right. I remember John Doar talking about that. And we’re probably using a bastardized version of objectives, as is everybody else.

I need to go back and look at that again. Well, great. Well, let’s go back to the strategy.

I think one of the key things in the playing to win construct is you start off with this idea of what’s your aspiration? And then where are you going to play?

And so I think defining your kingdom the way you describe it is one way of thinking about where you’re going to play. Can you talk through some of the considerations and vectors that you help people explore?

Tami Reiss

00:18:49.040 – 00:19:03.464

I like to generally work with companies that already have product market fit, but I coach a lot of clients who aren’t necessarily there. And so first of all, you have to recognize through a variety of metrics whether or not you’re there right now.

Randy Wootton

00:19:03.512 – 00:19:23.628

So tell me that, because I do think that’s one of those concepts. Do you have product market fit? That there would be a lot of debate.

There’s a great guy out there, Bruce Cleland, who wrote a book, crossing the not crossing the casino. Oh, shoot. It’ll come to me. But he talks about having category alignment before you have product alignment. But go ahead.

How do you define product alignment?

Tami Reiss

00:19:23.724 – 00:19:27.852

I would agree with that. Category alignment. For product alignment, there’s lots of alignment. You have.

Randy Wootton

00:19:27.876 – 00:19:30.440

Okay, lots of alignment, but, okay, lots of alignment.

Tami Reiss

00:19:30.860 – 00:20:23.004

Finding product market fit is not a one day task. Ostensibly.

Like if we talk about a vision of what product market fit means, it means that there are a group of people, aka the market, that have similar problems, and those problems are insufficiently solved at the moment. And you are offering them something that they are excited to give you money for because of how you solve their problems.

And there are enough of them that have already chosen to give you money. They have lasted a cycle or two. They continue to give you money.

And a number of them are so excited about the value you provide, they’re willing to tell other people about it. And that is the plain english definition of six referenceable customers.

Randy Wootton

00:20:23.172 – 00:20:53.890

That’s perfect, because I do think a lot of people lose focus on the fact that initial sale does not mean product market. Fitzhen. They need to go through a cycle, go through a renewal cycle, and hopefully see some upsell.

And it’s got to be more than your mother and your best friends are buying it. Like there is a set of folks.

And that you have spent the time to understand what is the commonality in either their industry, their size, the problem. So now you start to really codify that what I loved in our pre brief is you said, who do you want to get a thank you note from?

Tami Reiss

00:20:54.270 – 00:20:54.654

Yeah.

Randy Wootton

00:20:54.702 – 00:21:24.000

And what would they say?

And to your last point, who are your raving fans that give you a sense of, now you’ve nailed the product a problem in a way with your product, that they’re delighted to pay you what they pay you. I mean, you got to be charging for it too. It can’t just be free. They’re investing time, money and those early adopters, enthusiasts. Yeah.

Social capital. And I thought that was a brilliant idea. What are they saying thank you for? Because that’s the pain that they’re really.

Tami Reiss

00:21:24.580 – 00:21:39.400

Who write you a thank you note that you would actually potentially like either post in your slack channel or your teams channel or post like put on a wall or that you would forward out to the whole company and say, look, we’re getting there, we’re doing the thing.

Randy Wootton

00:21:39.520 – 00:21:59.690

So with that, you talked about one of your things in defining your kingdom. We’ll come back to is this idea of a North Star metric.

So what is that how this dynamic we’re talking about, you got a set of customers, six referenceable customers. How do you take that to then create a North Star metric? Or I do.

You wait for a while until you have 100 customers, till you get the North Star metric. How do you think about landing that?

Tami Reiss

00:22:00.190 – 00:23:03.034

I think North Star metric to me is about some sort of usage that’s attached to this problem you’re solving. Right? So if you are, let’s be docusign, right. It’s number of contracts per person that are like being signed or total number of contracts.

I’d probably do total number of contracts. Cause for Northstar metrics, I don’t really like ratios. Ratios are perfect for actionable metrics.

But the North Star metric to me is something that should be constantly increasing with every customer. It should increase, thus getting bigger. Customers should increase it more. When a customer stays with you longer, it again should increase.

And it should be something tangible that the teams all understand. This is something of value to our customers. So that could be contract signed. I have a client who works in the construction business.

So it’s like number of plans that have been created, right? Number of projects that have been created.

Randy Wootton

00:23:03.082 – 00:23:07.910

And it’s something other than revenue. It’s tied to something other than some way that they’re interacting with your product.

Tami Reiss

00:23:08.450 – 00:23:10.090

It’s generally correlative, right?

Randy Wootton

00:23:10.130 – 00:23:10.714

Oh, quarterly.

Tami Reiss

00:23:10.762 – 00:23:12.826

Because it’s correlative.

Randy Wootton

00:23:12.978 – 00:23:14.930

It correlates. Got it correlates.

Tami Reiss

00:23:14.970 – 00:23:22.960

Right. In that. Like if we are delivering this and this is going up, it should translate into more business value too.

Randy Wootton

00:23:23.260 – 00:24:41.978

You know, it’s funny you bring this up, Tami, because one of the debates, well, from Maxio, selfish advertising for Maxio, right. We do billing invoicing for B, two B SaaS companies.

What we find is they often have one of two go to market models, a PLG product led growth model or an SLG sales led growth model. They have one of two pricing models, either fixed rate or usage based, and many companies will have hybridization.

And it’s been interesting to see the debate. Mark Benioff, for example, came out. I think it was him just recently who said, look, the old user seat model for charging is going away.

Everything is moving to usage. And so I think what you’re alluding to is if you get the northstar metric right, that’s also a way you could charge for it.

So there’d be direct correlation. If you can create value associated with the usage in the customer’s mind, it may be a ties back. And what are they saying? Thank you for us.

Hey, billing and invoicing work, they didn’t have any issues. So it’s number of issues, number of invoices delivered without an issue or something along those lines changes. Okay, well, great.

So Tami, we were talking about the doorstar metric and usage and how to think about driving value.

And one of the things this informs is you talk about under your kingdom is your product strategy and this idea of how do you think about new ideas for products you had framed these two vectors to consider. Can you tell us a little bit more about that?

Tami Reiss

00:24:42.074 – 00:25:13.912

Yeah. So first of all, the promise of SaaS is that your product is always going to get better, right? Right. It’s why someone’s paying for a subscription.

So you always have to keep that in mind. So there has to be something you’re doing to enhance your product for your current market.

Your current users are paying you on a monthly or annual basis, because theoretically you’re going to serve them more, solve more of their problems.

And so if we have our current market and our current customer base, and that’s our kingdom, we might have a defensible mode around it, all that fun stuff.

Randy Wootton

00:25:13.976 – 00:25:14.820

Big wall.

Tami Reiss

00:25:15.660 – 00:27:08.228

We have an option of going in two directions, direction. One is towards cross sell.

We know our market very, very well and we want to offer them new things, whether that’s new features that might be an upsell or full cross sell, that it’s an entirely new product. But hey, we understand you. We understand your problems. And currently we handle a, B and c, but now we’re going to handle d, e and f.

And we would love for you to take our FP&A software and also use it for product market fit, cash flow modeling or whatever. I don’t know. But something, right, you’re expanding what you can do. And so that is same market, new product or new features.

The alternative is same product, new market. So you’re not really changing your product very much, but you might be changing your sales motion going up market.

You’re gonna have an enterprise sales team going down market. You might start PLG motions going geographic expansion or otherwise, but you’re not changing your product very much.

You’re just saying, hey, there are other companies or other whole teams within a company that could use our product that we didn’t think about before because they were in our ICP and it turns out they could use us. And this is what Zendesk is doing right now. So they said, hey, we are like a premier customer service platform.

But it turns out what that really means is that we help people send templated emails and help people manage that and share who’s going to respond and all of these sorts of things. And the other group of people who also needs this is sales teams.

And so now they have Zendesk for sales and it’s a lot of the same backbone thing, but they’ve adapted a little bit, but not very much. But it’s a brand new market for them. The entire sales team budget is all of a sudden available to them. Huge new TAM, right?

Randy Wootton

00:27:08.284 – 00:28:04.568

Yeah, that’s interesting.

I think I was working as strategy guy, strategy officer at seismic after I sold percolate to them and we engaged Bain to help us frame our broader m and a strategy, and then specifically due diligence and they created this great template for us to use.

And on one dimension was user buyer similarity, on the other dimension was software similarity and that included both workflow flow and integrations in the ecosystem. So very similar to you. And we use that to inform if we were to look at the next adjacency that we would go after, was it to stay within our core?

In this case it was sales enablement or would we extend for Maxio, are we selling to primarily the controller or how would we extend to FP and a, what would that look like?

So I think that model that you’re talking about and being deliberate and in our pre brief you had talked about and be intentional, should only go once, one direction at a time, especially when you’re small, super hard, one direction at.

Tami Reiss

00:28:04.584 – 00:28:11.776

A time for sure. And also there’s this third option called new market, new product. I call that the red zone.

Randy Wootton

00:28:11.848 – 00:28:12.248

Okay.

Tami Reiss

00:28:12.304 – 00:28:21.120

Stay away from the red zone. If you are not knowledgeable about the product and you are not knowledgeable about the market, that is like a brand new company.

Randy Wootton

00:28:21.200 – 00:28:44.080

Yeah, that’s right. So let’s use that as a way to segue to the second part of the conversation of why you need a coach. You’ve been doing coaching for a while.

You’ve been in it very deliberately for the past four years. How do you convince someone like me, a CEO, that either I need you as a coach or I need to hire you to coach my product leader? What’s the pitch?

What do you find when you’re working with people that are the things you help with them the most?

Tami Reiss

00:28:44.820 – 00:29:14.780

So I have unique background in that. I was working with an insight partners and their portfolio of companies. At the time, I think there were 175. Now there are over 500 companies.

And so I have a unique perspective on seeing hundreds of companies, whether it was at insight or at pivotal labs or when I was a consultant. And so my coaching comes from lots and lots of data points and my trend recognition software, also known as my brain.

Randy Wootton

00:29:15.920 – 00:29:18.496

Your pattern matching. Yeah, totally pattern matching.

Tami Reiss

00:29:18.528 – 00:29:23.584

Right. The reason why you hire a coach is to see things and surface things you don’t see.

Randy Wootton

00:29:23.672 – 00:29:38.706

What do you find product leaders broadly, are not seeing?

Do you have patterns there that you, when you walk in and you help them do the assessment of the organization and the processes and the systems, the talent in general, what are product leaders missing that you’re able to help them?

Tami Reiss

00:29:38.898 – 00:29:56.130

Number one is they don’t know what their goal is. They think their goal is to get budget for something or to get headcount for something, etcetera. That is not their goal.

Your goal is always, in every interaction, to be building trust and confidence.

Randy Wootton

00:29:56.430 – 00:29:57.150

Okay.

Tami Reiss

00:29:57.270 – 00:29:59.050

And so that’s a big.

Randy Wootton

00:29:59.630 – 00:30:02.430

Sorry. Is that with customers, with the negatives.

Tami Reiss

00:30:02.470 – 00:30:17.164

With co workers, with the CEO, like, every interaction you have with your coworkers, with, like the CRO, is making sure they trust you as the person who leads one of the biggest resource teams.

Randy Wootton

00:30:17.262 – 00:30:17.744

Interesting.

Tami Reiss

00:30:17.792 – 00:30:18.024

Right.

Randy Wootton

00:30:18.072 – 00:30:20.216

Okay. All right. That’s number one. What’s number two?

Tami Reiss

00:30:20.328 – 00:30:23.688

Number two is that they don’t understand how political things are.

Randy Wootton

00:30:23.784 – 00:30:30.016

Does that depend on the size of the company, the culture of the company, or is that broadly across all companies you deal with?

Tami Reiss

00:30:30.208 – 00:31:08.748

I think broadly across all companies, there is some level of politicalness, right. Where someone is trying to get more budget for their own stuff. Right. And they are taking steps that will allow for them to do that.

And you have to do whatever feels authentic to you, but be aware of what might be happening around you. I work with a lot of product manager.

Sorry, product leaders who, they’re first time product leaders, and they don’t understand the relationship they need to build with the CRO who might be saying, oh, products not doing things. Right. And that’s why I can’t sell how.

Randy Wootton

00:31:08.764 – 00:31:35.548

Does that translate into the politics if sales is saying, hey, I mean, it’s classic, right? Sales and marketing do this. Sales, marketing and product do this.

But what help me understand is that because the salesperson is saying, okay, I need to spend more money on salespeople because the product team’s not working, or like, don’t give the product people more resources. Or is it the flip side, which is, hey, product’s not delivering.

So we actually need to invest more in product and engineering to get more capabilities.

Tami Reiss

00:31:35.604 – 00:31:49.712

I wish that was the case. The case you didn’t mention is sales says products doing all this discovery work and we know exactly what they need.

We know exactly what the customers need. Why don’t you just let us tell product what to do?

Randy Wootton

00:31:49.816 – 00:31:54.704

Okay. So it’s the prioritization, the roadmap conversation that sales is like, if they only.

Tami Reiss

00:31:54.752 – 00:31:56.360

Built this, we told them.

Randy Wootton

00:31:56.440 – 00:33:06.962

Right. Got it. Okay. I’ve never been part of that.

And I do think, I think that is one of those great points you’re making in terms of coaching product leaders. How do they set up their listening posts with sales and with cs?

And how do they become transparent in the way they set up prioritization and try to tag both dollars and logos to different capabilities and then force rank it with the entire team?

Because in as well as thinking about not just the horizon one capabilities you need to bring, but also the horizon two and Horizon three capabilities you need to be building.

And that’s the unique perspective that the product managers, they’re doing their jobs like we were talking about earlier, and they’re out talking to customers, they’re understanding what’s happening in the landscape because they go to conferences, they talk to analysts, they’re able to say, oh, these are the broader trends in the market and we need to intercept these. And so how do you balance those three things?

And then I think the product leader leading that conversation at the executive team on a regular basis and with the board, like, here’s the product strategy. It’s aligned with the corporate strategy, but here’s the product strategy. And these are the bets we’re making.

These are the investments we’re investing is where you can have those conversations.

Tami Reiss

00:33:07.026 – 00:33:17.746

Yeah. And so this is actually a meta coaching. Right.

So I coach the product leader to be aware of this, but I also coach them to help their product managers do the same thing.

Randy Wootton

00:33:17.778 – 00:33:18.514

Yeah, right. Totally.

Tami Reiss

00:33:18.562 – 00:33:51.296

Because they are a reflection of the product leader.

And so the product leader has to coach their employees and say, you need to set up listening posts with the onboarding team you need to set up listening posts with the platform team or whatever else, and emphasize to them that they are also building trust and confidence in the entire product team and the product way of working, etcetera. Right. And so that’s a big thing.

There are other things, but the only thing I would really mention is that not enough product leaders understand that if m and a is happening, they want to be involved.

Randy Wootton

00:33:51.408 – 00:33:55.704

Hmm. Okay. Be in the know. Absolutely.

Tami Reiss

00:33:55.752 – 00:34:11.112

Be in the know. Whenever it starts happening at your company, just be a fly on the wall. It is a unique opportunity, but it happens so often.

And the more you know about m and A and inorganic growth, the more valuable you are to other companies.

Randy Wootton

00:34:11.216 – 00:34:38.862

Amen. And I think especially for PE firms, I think if you’re, if your sponsors, PE firm, they’re all about organic and inorganic growth.

Or if you’ve hit that threshold of $50 million, you. They want to see continued growth. Your core growth is going to move at whatever it’s going to move.

But then you need a layer inorganic growth to drive growth. But also, I think at that stage, you’re approaching that hundred mil and you can get bought by another PE firm or strategic.

One of the capabilities they want to see is that you can do m and a. Yep.

Tami Reiss

00:34:39.006 – 00:34:59.470

So, yeah, absolutely.

But if you’re a SaaS company, that’s at around 50 mil, and all of a sudden you’re thinking about whether or not you should uplevel your vp of product or hire in a CPO. One of the biggest reasons you’re going to choose to hire in a CPO from the outside is because the VP of product you currently have has no money.

Randy Wootton

00:34:59.550 – 00:35:01.038

Ah. So there you go.

Tami Reiss

00:35:01.054 – 00:35:11.198

And you’re about to embark on those sorts of things. And you can’t handle the potential, like, mishaps that might happen from a novice.

Randy Wootton

00:35:11.254 – 00:35:33.966

All the risks around integration, creating a plan, consolidating teams, roadmaps considerations. Absolutely. 100% agree. All right, well, let’s shift to the final topic. Tami, speed rounds. So, three, three questions.

One, what’s your favorite metric and why? Number two, favorite book, other than your book on what was it? Oh, shoot. Product manager.

Tami Reiss

00:35:33.998 – 00:35:35.478

Product manager. What do product managers do?

Randy Wootton

00:35:35.534 – 00:35:41.770

That’s right. What do product managers do? So, other than that one, and the third one is favorite influencers and why? So, favorite metric?

Tami Reiss

00:35:43.040 – 00:35:44.544

Net revenue retention. Nr.

Randy Wootton

00:35:44.632 – 00:35:48.384

And why that versus gross retention? Sometimes people will argue gross retention.

Tami Reiss

00:35:48.552 – 00:36:21.926

To me, net revenue retention says, we had 100 customers before they were giving us $10 million. And next year of that $10 million, how much of that is left, plus how much of it is expanded.

And so in A, B, two B, SaaS World, like Star, red, like gold Star, companies are at 120%. Right. And it’s your way of saying, we know how to land and expand, we know how to maintain our customers, but also have them grow.

And so that’s why I love, I.

Randy Wootton

00:36:21.958 – 00:36:31.742

Thought the other thing was that NRR is a classic product management metric because you’re able to sell in the additional products. Right. You get those upsells and so tie with that. But, okay.

Tami Reiss

00:36:31.806 – 00:36:37.286

But it also falls back into the idea that, like, your first sale with a customer is always going to be the hardest.

Randy Wootton

00:36:37.318 – 00:36:37.904

Yeah.

Tami Reiss

00:36:38.062 – 00:37:00.684

And so if we as an organization are placing the right amount of investment in account management and in CS so that people can learn about the new products and features that are available, they might increase the number of seats they’re using with us or increase their usage. Right. And so that, to me, is what it’s really showing, and it’s a very holistic vantage point that everybody can be involved in.

Randy Wootton

00:37:00.772 – 00:37:37.566

I think a lot of people don’t spend a lot of time disaggregating the metrics that lead to NRR.

For example, taking customer acquisition costs and from a blended view to new versus expansion and allocating costs for marketing and customer success.

And it does often look better and easier because you already have, you have a spa in place, you’ve gone through procurement, you’ve got a point person who’s probably a champion.

But even in these days, what I’m hearing was there is an over rotation to try to drive customer sales, but everyone was tightening their budget, so we haven’t seen as much purchase as well. But I think it’s a great metric. All right.

Tami Reiss

00:37:37.678 – 00:37:58.232

And this also is a great opportunity for PLG. A lot of people think of PLG as only self service, initial enrollment.

But in fact, PLG can also include the motion towards upsell, cross sell within the product. Right. And contributing towards NRR without having an account manager or at least teeing it up for the account manager, etcetera.

Randy Wootton

00:37:58.286 – 00:38:00.628

That’s great. All right. Favorite book.

Tami Reiss

00:38:00.804 – 00:38:09.860

I love crosses. Never split the difference, because it’s all about interpersonal communication to get what you want and not about compromise.

Randy Wootton

00:38:10.020 – 00:38:12.880

Okay. Remind me not to negotiate with you.

Tami Reiss

00:38:13.540 – 00:38:26.916

Oh, I’m not that great at the negotiation stuff. I just, I like, I wish I could negotiate like a FBI hostage negotiator, you know, and make sure I get the people home, but.

Randy Wootton

00:38:27.028 – 00:38:40.380

All right, given the time, pick one influencer. You have three that we talked about Simon Sinek, Brenny Brown, and Leah Taren.

Which of the three do you like best and want other people to follow and learn from?

Tami Reiss

00:38:40.500 – 00:39:38.720

All right, so I think enough people are following Simon Sinek and Brene Brown and know who they are. But Leah Theron is someone who’s especially for your environment, someone people should be more aware of.

She is a PLG expert in all senses of the world. This word specifically in B two B SaaS.

And if I had to summarize a lot of what she talks about, it’s that PLG works best with collaboration, that it’s product and sales working together.

It’s product and customer service and sales working together to create PLG motions that are automated, that are product assisted sales, and that especially in a B two B environment, it’s never going to be one or the other.

And that when you get back to what we were talking about to begin with, which is we’re all on the same boat trying to accomplish the same thing, you don’t get as mad about, oh, this is going to come from product or this is going to come from sales because the pie is big enough.

Randy Wootton

00:39:38.800 – 00:39:40.552

Yeah, that’s great.

Tami Reiss

00:39:40.616 – 00:39:42.832

The main thing is that the company’s growing.

Randy Wootton

00:39:42.896 – 00:40:33.686

Yeah. It’s something that we’re not doing well yet. It’s hard to move from a company that’s. Look, we have lots of flexibility.

We allow for people to bring in their established processes. What that means, though, is it requires implementation.

So I think it’s hard for people that have one of these more sophisticated tools to slim it down, to make it valuable in a PLG motion, which is usually free out of the gate or trial or freemium that then you upsell folks. So we’re exploring it. I’ve been reading and working with a guy named Dave Boyce, who was the. I think he was a founder of winning by design.

He’s writing about PLG. There’s some other folks, so I will certainly add Leah to my list to go learn more about it. So thank you.

Thank you for that recommendation, and, Tami, thank you for your time. I’ve really enjoyed the conversation. It was great to spend a little bit more time with you.

Tami Reiss

00:40:33.798 – 00:40:36.974

Yeah, my pleasure. I would actually, if we have just 30 seconds.

Randy Wootton

00:40:37.022 – 00:40:37.446

Sure.

Tami Reiss

00:40:37.558 – 00:40:40.414

I want people to know why they should hire a coach.

Randy Wootton

00:40:40.502 – 00:40:40.870

Okay.

Tami Reiss

00:40:40.910 – 00:41:25.230

So as you advance in your career, you cannot turn to your boss for advice, either because they’ve never had your job or because that will again lose trust and confidence. And it is good to have a sounding board.

So if you are at any point in your career where you’re feeling like you want to advance but you need something more than your boss. Who’s going to hold you accountable? Who’s going to see the field right and tell you how to adjust your actions to accomplish your goals.

That’s when you want to hire a coach. And that could be a sales coach, a business coach, a product leadership coach, an interview coach.

There are so many different kinds of coaches out there, but the main idea is that it’s someone on the outside who’s invested in your progress and your growth and nothing more.

Randy Wootton

00:41:25.310 – 00:42:32.180

100% agree. In fact, my, I think it’s a leadership principle. Number seven, or secret of success is investing in your tribe.

And I frame it as your mentor, a coach, an advisory group like a vistage or YPO or EO and then a personal advisory board. People you go to who know who you are and call you on your b’s.

But the distinction I draw between a mentor and a coach is a mentor for me is someone who’s been in the situation you’ve been in. They’ve led turnarounds at, you know, $20 to $100 million companies B, two b SaaS or their finance executives.

The coach for me was, I asked for one when I first started at Rocket fuel to help me learn how to manage the board. So it was more about interpersonal effectiveness and managing the stakeholders and all that.

And so I do think being deliberate about what are you investing in as a leader, CEO or product person to continuing to your point, like just have someone who’s on your side and there is no other agenda other than to make you great, make you your best self is why people should look at coaches and get companies to invest in those coaches.

Tami Reiss

00:42:32.640 – 00:42:33.808

Couldn’t agree more.

Randy Wootton

00:42:33.944 – 00:42:37.384

Awesome. Well, with that, we’ll wrap it up. Thank you so much for your time, Tami.

Tami Reiss

00:42:37.472 – 00:42:39.120

Thank you. Thank you for having me.