Transcript

Ops and Sales Leadership: Two Vital Responsibilities

[0:00] There are two things that ops cannot do for you. One is be the police.
Sales leadership needs to be the police.
And the second thing they can't do is build process in a vacuum.
Welcome to the Full Funnel Freedom podcast. If you are listening to this, you are likely leading a team responsible for generating revenue.
Purpose of Full Funnel Freedom is to support people like yourself and keep your.

[0:30] Music.

[0:30] Funnels consistently, reliably full.
Welcome to the full Funnel Freedom Podcast. I'm your host, Hamish Knox.
Today, I am delighted to have Taft Love as my guest today.
Taft is the founder of Iceberg, a sales and marketing operations agency that helps growing companies transform their go-to-market operations.
Before tech, he was a police officer, a federal investigator, and a sales guy. Today, he lives in Austin, Texas, likes flying airplanes and perfecting homemade pizza when he's not spending time with his family.
Taft, welcome to Full Funnel Freedom.
Hey, thanks so much. I appreciate you having me. Yeah, it's great to reconnect with you.
And so I've given the audience, you know, the 30,000 foot view, who you are.
Tell us the story of Taft, where you came from, what you're doing now, where you're going.

[1:21] Take us away. You got it, man. I'll go deep here. Small town, North Carolina, grew up, was a cop for a while, about almost 10 years, and went overseas for a little while.
And when I came back, I kind of fell ass backwards into a sales job, cold calling as an SCR for a small SaaS company.
Got the job off Craigslist, had no knowledge of SaaS or startups or anything.
It was just like somebody who would hire me to do something. Wow.
And that sort of snowballed into this career that I've been really fortunate to have now that spans startups some people have heard of, PandaDocs, SmartRecruiters, Doxin, which was acquired by Dropbox, and my current gig is founder of Iceberg.
And so that, I guess, is worth kind of double clicking into that, which is… Thank you.
Yeah, I was an SDR and then an account executive.
And it was at Pandadoc where I figured out, Hey, I can't be successful with what exists here.
And I think every sales guy at every small startup, sales guy or gal at every small startup has felt this before.

[2:36] You really don't have the tools when it's... You just graduated from founder selling into being early salespeople and marketing people at a startup.
And not because anybody is not doing their job. There's nobody at fault here.
You just don't have the systems around you to be successful.
And so I sort of became the ops guy at PandaDoc.
And that straddled sales leadership and operations leadership for years after that. I did the same thing at Smart Recruiters.

The Intersection of Sales and Operations: A Virtuous Cycle

[3:11] At DocSend, I was pretty pure sales. and then a Dropbox ops again.
And so that's been my path since, is sort of straddling these two worlds.
And frankly, they reinforce each other. It's a virtuous cycle.
If you've been in seed as a sales or marketer, then doing RevOps is much easier.
You have the empathy that pure ops people might not have.
Very fair. I once did a talk called Sales is from Mars and Operations is from Venus.

[3:40] And this was years ago. And it went over really well because it was a room full of CEOs from a bunch of IT companies and they're like, yep, that's pretty much how it works.
So clearly you saw a gap in the market, right, to straddle these two.
So where should we start in terms of this making sales and operations actually coexist, you know, not just in a sort of a detente fashion, but like, hey, we like each other. We're here to support each other.
What's the first thing that we should be considering as sales leaders when we're thinking through this process? Yeah, I think two super high-level pieces of advice for sales leaders, because at most small startups, sales has more budget than anyone else.
They're the ones who are first able to pull in an ops hire or an agency to do ops for them.
And that's fine. You don't need a true rev ops function when you're really small.
You just need whoever can get the freaking job done.
And so the 2 things I would say you should do is first, hire ops people who either have deep sales experience, or have deep experience sitting with the sales team and understanding how they work.
Because sales and ops that don't talk to each other and don't work together literally sitting together at the same desk and watching where someone clicks.

[4:53] If you don't do that, you're already at a huge disadvantage.
And the second thing is invest in operations early.

Defining Ops: Process and Systems for Sales Enablement

[5:01] The longer you crowdsource and figure out ops on your own, even if you're very, very smart, the more likely you're building massive technical and systems and process debt that you're going to have to pay off down the line as the pressure builds.
When you have a board breathing down your neck, and you can't get them the numbers they need, that is not the time to start thinking about getting your first Ops resources together.
Yeah. Eventually, the Franken stack that we've built is going to completely fall apart, right?

[5:33] So let's define Ops very quickly. Because when we talk RevOps, we talk like Ops can be as big or as small as we want it to be.
Right now, you're clearly helping founders with their go-to-market motions, right? So what, in your world, or what would you recommend we start with for Ops, quote unquote?
Earliest version of Ops, despite what all the gurus tell you about what Ops should be and how it should work, the earliest version is people who design process and implement systems to support those processes.
That's it. That is Ops in a nutshell.
It will grow into owning more and more over time.
Ops becomes enablement. But honestly, if you've just hired your first sales team, you're a brand new VP of sales.

[6:20] Dude, you need to own enablement, you need to be able to train those reps, you can't go tack that on to operations.
And similarly, finance like sales finance, the VP and the CEO are just gonna have to get together and model out what's coming for the next year for their board, you probably don't have the money to go hire a qualified sales finance operations person to be part of your rev ops program.
So early on, process and systems, and that's it.
And then it grows to sort of swallow these other tangentially related operations functions that your first couple of years can just live with the leadership. Fair enough.

Sales Leaders Must Own Ops and Establish Processes

[6:57] Ultimately, there could be a temptation for a new sales leader to be like, I'm just going to abdicate, just push that over there.
But ultimately, what I'm hearing from you is, as that sales leader, we got to own it, and then we've got to get the processes and systems in place before we start all the other fancy stuff that is eventually going to come when we transition to enablement. Is that accurate?

[7:17] That's exactly right. Look, if you wanna do sales, if you just wanna run deals and manage people and be a pure sales leader, then go to a thousand plus person company and go to a place where everyone is a cog in a well-run machine.
If you wanna work in early stage land, you are many, many things.
And every single one of those you decide to outsource is a huge risk for you.
And so be very careful about which ones you hand off early to people who you're able to afford when you're at 5 million, 10 million run rate.
Fair enough. So first place, we got to get an ops function. We've got to get systems and processes.
All right, now let's build this out. So yay, we're starting to scale.
Yay, our salespeople are sitting next to ops. They love each other. What happens next?

Importance of Documenting Processes for Scalability and Success

[8:09] Next thing you need to do is write down what people do.
Everyone skips this. You're moving so fast. It's all institutional knowledge.
And then the wrong person leaves, and suddenly, everyone is screwed.
So write it down. And this does not have to be particularly difficult.

[8:27] There's so much tech now. And I am not a tools-first guy.
This may come out more as we talk. I'm not a tools-first guy.
But there are some really interesting things happening in the market right now where these these teams rattle is a good example, that are combining the building and the documentation in a single tool.
So like the interface you use to build a process serves as your documentation.
So it's getting easier and easier and easier to write down how things are supposed to work and what the various systems are doing within these processes.
And even if you don't have a rattle, like, get a mirror, get a lucid chart and just draw what is happening.
So So that's the next step, which is sort of a precursor to true enablement.

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Fair enough, yeah, we coach the leaders that we work with. Just do one thing, like put one thing down.
It doesn't not have to, you don't have to go lock yourself away for three days and come back with, you know, very current reference, a phone book's worth of documentation.
Just one thing, just one thing gets the motion going.

Building Documentation: Best Practices and Mistakes to Avoid

[10:01] So when we're looking at documentation, Who should that documentation?
Come from? Like, are we going out and interviewing our top reps and going, hey, how do you work through these motions?
Or are we making it up out of our own head about what our ideal state should look like? Where do you see the best practices coming out from documentation standpoint?

[10:23] There are two things that ops cannot do for you. One is be the police.
Sales leadership needs to be the police.
And the second thing they can't do is build process in a vacuum.
So everybody makes this mistake, me included early in my career.
You decide how everything should work, you design it, you build everything around it, and then you put real humans in it who don't do it.
And it reminds me of, there's this image, and I've struggled to find it in the past few years, but it's like the perfect representation of an ops mistake.
It's this path with a gate covering the path.
And then in the grass, it's worn where people have just like walked around the gate and nobody goes down the path as it was designed.
And that is what happens when you build in a vacuum.
And so if you started out right, like we talked about, ops people come in and they build deep empathy for what sales is doing and why, and what are the, out. Cheers, dude.
Everyone is responding to some incentive when they have a behavior.
Don't ignore that and don't decide that just saying that we do things differently is actually going to lead to different behavior.

[11:38] What you should be documenting is what is happening today, and then nudge that behavior with aligned incentives in certain directions versus what most startups do, and in fact, a lot of big companies do, which is, we're throwing out all this behavior. Here's what we do today.
Then you come back a month later, and now the same thing's happening.
It's just not recorded in the systems because the systems are built for something we're ignoring. 110 percent.

Addressing Pain Points in Sales Operations

[12:05] Let's dive into that a little bit deeper. Let's say we've got a sales leader who's listening to this, who is thinking, I'm a couple of stages past where Kaft is talking about, and I'm feeling a lot of pain right now.

[12:21] In terms of the rescue squad, if you want to call it, where would you coach a sales leader to start looking in their op side if they feel a little bit of pain right now based on the things that you've shared with us already?
You have three choices. One of them is just plain wrong. Two are good in my opinion.
The wrong choice that so, so many pick is, hey, I've got this SDR who's kind of struggling at being an SDR, but she's really smart.
So like she can do that stuff. And I see it everywhere.
And Iceberg has It's made literally millions of dollars off of the cleanup post cleanup that was done by the person who didn't, who was very smart, but didn't know the answers to the task.
And so that's option one, throw it out. Don't do it.
It seems like a great idea and it saves you from having to let somebody go who's not working out but stop, don't do it.
The next two are hire a qualified in-house operations person to help fix this or hire an agency that specializes on whatever stage your company is in.
That is really, really important.
Focus on your stage. Do not come hire Iceberg if you are a Series D company that just raised $100 million and you need some help transforming a process that you have technical debt within. Go hire GoNimbly for that. They're like.

[13:46] Above market from us and really good at that. If you're a series A, you just raised your A, you're a year late in doing some of this stuff and you have technical debt but you're still small, you have 10 salespeople, call Iceberg or hire in-house.

[14:01] And there is no clean answer to which you should do it. It really boils down to what you're more comfortable with.

Hiring In-House or Outsourcing Sales Operations

[14:07] I don't think there's actually a wrong answer here.
The thing to remember is there's potentially more risk with in-house, if you hire the wrong person, you've got a six month time to like manage them out, hire someone else, get them spun up, stuff like that.
So we're easier to scale up or fire, but you're not building institutional knowledge when you hire us.
So there are pros and cons with each, but those are your three options.
And I'm happy to send you, if you'd like to have it as a link and ebook, we wrote about how to hire that first person, if you decide to do it in-house, Like literally, what questions do you ask them when you talk to them?
Perfect. Yes. We'll put the link to that in the show notes. So sales leaders, as you are listening, click the link, download the ebook and get some insights from Taft on how to hire that right person.
Because cost of a bad hire, I often use salesperson examples.
We had one leader work out, it was $2.2 million to recruit, hire, onboard, and eventually terminate a bad fit seller.
And the number I believe is somewhere between 4.5 and 6.2 times base salary for any role in the organization.
So sales leaders, think of a role in your team, multiply their base salary by 4.5 and then separately by 6.2. That's usually a lot of money.

[15:25] That we don't want to blow over. If we were gambling with that amount of money, we wouldn't want to gamble with it.

Transitioning from Sales Operations to Sales Enablement

[15:31] Download that link that will be in the show notes for you.

[15:35] We've got stage 1, stage 2. We've got a little bit of troubleshooting or what can we do here.

[15:43] Then how do we transition this from operations to enablement?
That was something you brought up earlier.
Eventually, ops becomes enablement. What does that look like and what does it mean to a sales leader? That's a great question.
I think enablement sort of takes two paths.
Once you start growing, enablement bifurcates into sort of technical, internal, ops-focused enablement.
What systems do we have? How do we use them? Where do you click?
So there's the sort of tactical enablement.
And then there's also a tactical element to this, but it's the sort of market enablement. How do we sell?
Who do we talk to? How do we talk to them?
They don't necessarily need two different owners. But generally, what happens is the first one happens first.
And then the second one, you, the first one gets its own hire first, the ops team starts doing that.
And the second one, the VP of sales and VP of marketing and their team sort of own that enablement, until you you're able to hire an enablement team.
And so I sort of I sort of think of these happening in two different stages.
But But in a perfect world.
Yeah, you're, you're long before you have a true enablement professional helping teach your reps how to teach you need somebody who owns just documenting what exists and where we click and how we do it. Right.
And then there are so many factors, it's hard to say there's a specific time, but usually.

[17:08] Late series A early series B is when companies in the SAS world or at you know, five to $10 million in the non SAS world of annual revenue get to a place where they're where they're hiring that dedicated sort of sales enablement person who's teaching sellers how to sell versus where to click.
Love it. Very, very cool. Taft, what is another warning sign that a leader should look for once they've got that resource in place?
You shared earlier, at some point, you have to do it, fair.
At some point, you're going to bring on somebody or you're going to have an agency. What would be a bit of an early leading indicator that this maybe is not working the way that it should be, that a sales leader should watch out for?
If you are not regularly frustrated because they're telling you no, you made the wrong hire.

The Cycle of Overusing Ops Talent

[18:00] Okay, say more about that. This is not what you do. Let me tell you a story about like the horrible cycle that we step into over and over and over at Iceberg to fix, to break.
And so let's take that early SDR who wasn't doing well but she's really smart.
So you move her into an ops role and she goes and gets a Salesforce admin certification, and gets a few HubSpot certifications.
And she's really sharp, even though she's never done this before and doesn't know the answers to the test, what's gonna happen in almost every scenario is you are gonna start using her to speed up all of the things you were doing before.
And she's not telling you no because the dynamic is not one of partnership, it's this person is now doing things faster than I can do it myself, but it's still making manifest my vision as a non-ops person.
And you're gonna notice they're firefighting a lot, but nobody here, it's the blind leading the blind.
You as the VP of sales, don't understand why the firefighting is happening.
You just know things are breaking a lot.
And you know that when you point her to it, she's smart. So she goes and fixes it and that fires out and yay, she's the hero.
And she is incentivized to do two things, work quickly and firefight.
She gets pats on the back for both of those things.

[19:20] And what she does not get kudos for is the thing ops team should be doing, which is saying, hey, everybody, time out, stop.
Why are we firefighting? Why is this thing breaking over and over?
Where is there misalignment between process and systems and reporting?

[19:37] And so a qualified head of ops, I wrote an article a couple of years ago that was something about how the the most important skill for for an ops leader is saying no. And.
You really have to be able to treat the people at the executive level around you as a partner.

[19:57] You have to be willing to prioritize and force their prioritization.
And you have to have your own vision for how this should all work together that allows them to assign you outcomes and not tasks.
So if you're assigning tasks to your ops person, even early stage, You don't have the right level and you are gonna...
Bill Gates has the quote about something to the effect of automating a bad process just makes the bad stuff happen faster.
And I butchered the quote, but that's the idea. Same with hiring an ops person.
You were making mistakes as a VP of sales that you maybe didn't even recognize.
And then you hire an ops person who's too junior and doesn't know the answers to the test or how to tell you no. all you did is pour gas on this dumpster fire.
Absolutely, yeah. And it really sounds like there's gotta be some humility and vulnerability on the part of the sales leader to empower that ops person.
Because ultimately, whether they are a brand new SDR or they've got decades of experience in ops and you bring them on, the leader has to be willing to hear no.
And if the leader's not willing to hear no, as you just said, we're just gonna pour gasoline on a dumpster fire. 100%.

Empowering Ops and Being Willing to Hear No

[21:13] So Taft, I'm digging this conversation because I love the human-to-human dynamic, and I love the fact that you're very focused on uniting two groups that are often, if not at war with each other, just sort of cold war with each other, and certainly could talk to you about this all day.
I do have a few questions before we wrap up, and the first one being, if you could go back and coach your younger self, right?
So go back to younger Taft and go, hey, Younger Taft, you're going to be the founder of this amazing company called Iceberg.

[21:43] You're also going to have a bunch of bumps and bruises and scar tissue.
What would you coach Younger self to do to arrive at the same place but with fewer bumps and bruises and less scar tissue?
I would say be less patient about the day-to-day and more patient about the long-term.
That was a mistake I made and I think a lot of people make.
You're impatient about the next promotion and your career advancement, and you're not sufficiently impatient about the task list that needs to be done today.
And so while it's counterintuitive, if you flip that, your career moves faster.
And so one is, yeah, be way more impatient about the day-to-day.
And I think, I take this from Josh Braun, who I just love all his stuff.
And the thing he says over and over and over again is disconnect from the outcome.
And that's true in sales with cold calling.
It's also true in operations. It's true in everything.

[22:42] Do the process well, do it right, and stick to it, and slow down and get it right.
And don't worry about whether the outcome was exactly what you expected, but sort of trust and respect the process.
And that also speaks to the patience thing. And so those are two things I think I got wrong early, that if I had it to do over again, I would allow my younger self to carry less stress and get more done.
Love it. Very cool. What an amazing answer. Other question for you.
What have you read, listened to, watched, whether recently or in your past that you would encourage our audience of sales leaders to check out to further their own development?
This is an interesting one because I have intentionally, lately.

[23:28] Stopped reading sales books and all of the...
I spent years packing my brain with stuff that I sort of questioned the value of overdoing it.
So I've been on a bubblegum reading spree that has actually helped free up a bunch of brain space.
Cool. And when I go back to sales books, the very first one I'm going to read is Jeff Gettemer's Little Red Book of Selling.

[23:56] I like that book because it is philosophical and reinforced something that I truly believe is super important with selling, which is be helpful and have a mindset of plenty.
If you do those 2 things, you're gonna succeed at sales.
Because being helpful takes more than just being a nice person.
Being helpful in selling means you have to be an expert. You can't be helpful if you don't know what the hell you're talking about.
If you don't understand their problems and their market and your systems or whatever you're selling and how they work together.
So be helpful and have a mindset of plenty. No commission breath.
Just like be there to help and people will buy more from you than otherwise.
So that's the book I would focus on if I decided to go back into reading sales books today.
Love it. Very cool. That is a great book. I've read it myself.
I saw Jeff speak here in Calgary several years ago and the big thing I took away from him is someone said, well, how can you – what time is it when you're traveling?
He said, well, I know it's called either daytime or nighttime and I know by looking out the window. And I was like, what a very good answer, Jeff. Well played, sir.
Uh, all right. Last question for you, Taft. Uh, you've given us so many great ideas and insights already on how to meld sales and operations together.
What do you have for a closing thought, a bit of wisdom or something to plug? The floor is yours.

[25:14] Awesome. Thanks so much. Yeah, the biggest thing I would say is, if you're interested in learning a little more about operations, a thing we're doing now is a completely free, hour-long session with me, not my team. I don't push this off on someone else.
You can sit down with me for an hour and talk about whatever operational stuff you're dealing with.
So if you're struggling with sales ops, come talk to me. You can go to our website, icebergops.com, fill out a form.
We're not gonna spam you. We're not gonna call you a bunch. You can just set a time to come talk to me.
And we will talk through whatever the hell you're dealing with and you don't have to buy from me. I hope you do. I'd love that, but you do not have to.
And we can leave with a game plan for you to go hire somebody to implement or do yourself or have us come help you with.
And so that's the thing I'd like to plug and otherwise invest earlier in ops and get good ops talent, it's worth its weight in gold.
Very cool. We'll certainly put a link to Iceberg's website in the show notes so you can quickly and easily access that if you'd like to get some of more of Taff's amazing wisdom.
So Taff, I've had a blast. I look forward to continuing our conversation offline.
Thank you for being a guest on Full Funnel Freedom today. Thanks so much for having me.

[26:31] Sales leaders, I had a blast talking with Taff today.
In my career, sales and operations, if they have not actually been at war, they've, you know, it's been a cold war, like I said in the episode.
And I really found that his insights on how to unite sales and ops, and especially from a sales leadership perspective, we can't abdicate this role.
And especially if we're in that early stage startup, or if we're into a larger company that maybe has never had an official ops or enablement program before.
We can't abdicate it. We've got to get in, figure out what needs to be done, what are the outcomes, and then bring someone on board.
I also want to reinforce that idea of we have to give our team members, and this is all team members, but we're specifically talking about ops today.
We have to give them the permission and the protection to challenge us and to say no to us, because ultimately we have an outcome, we have a target, we have growth, we have scale that we need to hit.
And also we hired our team members for a reason.

Empowering Employees to Push Back and Innovate

[27:34] So we need to give them the permission, the protection, the freedom, and the flexibility to be able to push back and say, hey boss, I get that you want to get to that mountaintop and you're telling me to do it in this way. There might be a better way to do it.
Or hey, I get that you just had a flash of brilliance in the middle of the night and you want me to completely adjust course.
I'm not going to do that because sticking on our path is going to create the motions that we want and the success that we're desiring.
So love to hear your takeaways in the comments on our social media and until we connect on the next episode go create full funnel Freedom.
Thanks for listening to today's episode of the full funnel freedom podcast You can continue to support us by leaving us a review and a rating Sharing this episode with a couple of sales leaders in your network who you care about.
I'd love to connect with you I'm easy to find Hamish Knox on LinkedIn Also, if you'd like a free 15-minute call with me, go to www.hamish.sandler.com forward slash howtosandler.
Until we connect on the next episode, go create full funnel freedom.

[28:42] Music.