Bobby Jaffari & Ian Faison 34 min

Leading with a Growth Mindset


On this episode, Bobby talks about aligning executive leadership around RevOps, understanding the company and customer journey, and why revenue operations is the glue.



0:00

Welcome to Rise of RevOps. I'm Ian Faison, CEO of Caspian Studios and today I'm

0:09

joined

0:10

by a special guest, Bobby. How are you? Good. Thanks for having me. Yeah,

0:14

excited to have

0:15

you on the show, excited to chat about Interible and all the cool stuff y'all

0:19

are doing from

0:20

revenue perspective, from a RevOps perspective and all that stuff. You've been

0:23

with the company

0:24

not super long. It's an exciting time to jump in right before that 90 day mark

0:28

to see how

0:29

it's been going in your approach to coming into the company. But before we get

0:32

into all

0:32

of that stuff, how did you get started in revenue? For me, it's been a long

0:37

journey.

0:37

It's spent about 20 years in what you would call now SaaS in various revenue

0:42

leadership

0:43

positions, leading individual sales teams all the way to running an entire

0:48

business segment

0:49

for a now public traded company to where I am today at Interible, running the

0:54

revenue

0:55

operations function within Interible. So it's been about a 20 year journey,

1:00

like I said,

1:01

multiple roles and functions primarily focused on go to market. And obviously,

1:06

I've seen revenue

1:07

operations evolve over that time as well. So excited to talk about it.

1:11

Yeah. So what's your definition of RevOps? Yeah, I think first of all, RevOps

1:15

is a what

1:15

I would maybe call a more recent, maybe last several years type of new

1:20

definition. Think

1:21

if we look back at least in earlier part of my career 20 years ago, you defined

1:26

it as

1:26

sales operations and you had finance operations function in a different part of

1:31

an organization.

1:32

You had marketing operations sitting within marketing. And I think as companies

1:37

evolved

1:38

and SaaS became the market that it is today, a lot of leaders started to look

1:43

at when you

1:43

look at revenue across the entire business, whether it's direct business,

1:47

indirect business

1:48

through channels, marketing and how all of these teams work together. I think

1:53

the revenue

1:54

operations role, which like I said, maybe you started as sales operations many

1:58

years

1:58

ago, evolved into what it is today is looking at the entire business, not only

2:04

go to market

2:04

business, but also from a finance lens as well, looking at all of that under a

2:10

lens of

2:11

how do you operate revenue across all of these different areas that businesses

2:16

drive their

2:16

revenue. And so for me, that's the evolution that I've seen happen. So I'll

2:21

pause there.

2:22

Yeah, we'll get into more in a sec how you think about building a RevOps team.

2:26

Zooming

2:26

out what is iterable do and who are your customers?

2:29

Yeah. So iterable is one of the most powerful customer engagement platforms

2:35

that enable

2:35

brands, brands that we all use every day to engage with their customers by

2:41

personalizing

2:42

data and communicating with customers in cross various channels. As an example,

2:48

someone

2:48

like DoorDash, all of us use at least I use DoorDash and significantly over the

2:52

last few

2:53

years. No, I don't use it. I got to say DashPass was like the ultimate save,

2:59

right? I have

3:00

a 18 month old kid and the wife and I. We've made use of our DashPass

3:04

membership that is

3:05

for sure.

3:06

Exactly. So what iterable does, we enable brands like DoorDash to understand

3:11

their customers

3:13

by understanding how their customers engage with their brand. So we look at a

3:16

lot of that

3:17

data and we understand the night step. For example, Ian likes to go out with

3:22

his family

3:23

and either go out to dinner or order dinner in. And so that we understand a lot

3:28

of that

3:29

data and then engage based on that personal level with you through email,

3:33

through SMS,

3:34

through push notifications, all of that stuff to various places. So we

3:38

basically enable

3:39

our brands to communicate with our customers in a personalized way.

3:43

Obviously coming into the role as CRO, how did you think about RevOps? What was

3:48

that a

3:48

priority for you coming into the role, thinking about how you wanted to build

3:52

your team? What

3:53

was your thought process coming into the job?

3:55

First of all, I'm the first CRO for iterable. And I think one of the reasons

4:00

for that is

4:01

as the business has evolved and as the business has matured over the last 10

4:06

years, there's

4:07

a lot of different avenues of revenue that have formed. You've got your direct

4:13

business,

4:13

new business side of revenue, you've got your channels and partnerships, you've

4:18

got your

4:19

customer success organization. These organizations were functioning great, but

4:24

they were functioning

4:25

in a very silent manner that were led by different leaders. And as the business

4:30

was looking to

4:31

go into that next stage of growth, one of the things that was important for

4:36

iterable and

4:37

for me was for someone to come in and take a look at the entire business, the

4:41

entire

4:42

customer journey from the time we market to them all the way to how we manage

4:46

that relationship

4:47

under one organization. And one of the biggest things for me, and I think for

4:53

iterable as

4:54

well, what was very important was what is the strategic function that enables

4:59

the revenue

5:00

leader to do that, to be able to understand the business as a whole, and that

5:03

is revenue

5:04

operations. And we folded revenue operations into the entire CRO organization.

5:09

And so for

5:10

me, and I can, whether it's at iterable or previously, when I was at my

5:14

previous company,

5:16

revenue operations was the most strategic function for me. It is my right hand

5:22

function, right

5:22

hand person, as I look at the business across all of the different various

5:28

functions and

5:29

how we operate the business and how we look at it, all the strategic decisions

5:33

we have

5:34

to make all comes with my partnership with my revenue operations organization.

5:39

So we

5:40

folded all of that into one organization so that we can have one view across

5:45

the entire

5:45

go to market motion.

5:46

Yeah. And so sales, marketing, sales ops, marketing ops and customer success

5:52

ops being

5:52

in one place. Or is there any turmoil of like pulling those out of those

5:56

individual functions?

5:57

Or is it you feel like that the important part there is to have it all in one

6:00

place so that

6:01

you in the whole life cycle?

6:03

Yeah, I think look, the people of iterable have been great, right? Not only in

6:06

the two

6:07

months that have been here, I've been speaking with the iterable team for

6:10

several months.

6:11

And so I think everyone has a common goal of we have to grow the business. And

6:15

so I

6:16

think everyone understood that why it's important to have this in one place.

6:21

That's number one.

6:22

But we also as a business as an entire business, we actually run a phenomenal

6:27

OKR process.

6:28

And so a lot of things that we do as a business, we align around our objectives

6:33

, our annual

6:34

objectives that we do and the quarterly KRs that we run. And so we get the

6:39

entire all

6:40

the GTM functions aligned around our OKRs. And it works generally well. I think

6:45

there's

6:45

obviously nuances between all of these different functions between like you

6:50

mentioned customer

6:51

success ops or marketing ops. I think ultimately revenue operations does

6:56

support variety of

6:58

different functions. So they have customers between different BU leaders like

7:04

our CMO or

7:05

our head of product event because we revenue operations also at iterable runs

7:10

business

7:10

insights. A lot of insights that we want to get for our product leaders will

7:15

come from

7:16

the business insights team. Not only the sales ops piece of it or the channel

7:20

ops or the

7:20

CS ops, but also broader business insights. It does certainly take a lot of

7:25

work for our

7:25

revenue ops leader to make sure that teams are aligned. But I think we do a

7:30

phenomenal

7:31

job of like I said, managing all of our business through the OKR process, which

7:36

has helped

7:37

keep everyone aligned.

7:38

So how do you think is it unique to your organization is this kind of I know

7:42

this is how you're

7:43

building it. But do you think that this is something that other CROs or other

7:46

rev ops

7:46

teams should mirror? Does it depend on your organization or is this sort of

7:50

like the best

7:50

practice that you see out there right now?

7:52

Yeah. Well, look, every organization is different, right? And my personal

7:56

belief is revenue under

7:58

one leader does make a significant difference. And so I think that's the

8:02

starting point of

8:03

getting the executive leadership team aligned around why that's important. And

8:09

then obviously

8:09

the revenue operations that glue that brings it all together. I do think that

8:14

when you

8:14

have a broad revenue organization, revenue operations organization in a

8:19

business, like

8:20

I said, that handles sales, marketing, CS and all of the business insights.

8:25

What I'm

8:25

learning, even an iterable for me is organizational alignment around our key

8:31

objectives, right,

8:32

that we want to drive. I think that to me, even in my two months here, I've

8:36

seen what

8:37

a different set makes. I think a lot of organizations aspire to do really good

8:42

OKRs. This is probably

8:44

one of the best places that I've seen it operate in my two months. One, I was

8:48

involved in last

8:49

quarters OKRs, but we're also in the process of FY 24 planning. So we're

8:55

defining our OKRs

8:56

for our at least our O's and KRs for Q1 of next year. And I mean, it's the

9:00

middle of that

9:01

right now. And I think that is the piece that is in my mind getting the

9:06

executive team

9:08

aligned around that makes a significant impact on just making sure that this

9:12

function, this

9:13

revenue operations function is tightly aligned to the company's objectives. And

9:18

I think that's

9:18

the piece to me that getting that alignment between the executive leadership

9:22

team makes

9:23

a big difference in how the revenue operation team operates.

9:26

Any interesting learnings in the first two months in terms of setting this up

9:29

or setting

9:30

up new rev ops team and corralling all those assets into one place.

9:33

As a revenue leader and as someone who prior to coming to Interval, I built a

9:38

business

9:39

for Freshworks that essentially in the Americas region, right, I let the entire

9:44

business as

9:45

president of Freshworks Americas, I built a business that was at the time when

9:50

I joined

9:50

about 35 million. And this year, Freshworks will be a 500 million dollar

9:55

business. Obviously

9:56

America's being 50% of that overall revenues, building your business from the

10:01

ground up

10:01

and understanding all of the strategic things you have to make a decision on,

10:06

right, how

10:07

you do segmentation, how you do territories, how you do your compensation plans

10:13

. Those

10:14

are things that I had to do in that previous role. And instead of just leading

10:20

a sales

10:20

team or leading a customer success organization, a lot of the strategies that

10:25

had to be defined

10:26

and executed of building that business really helped me get deep into the

10:31

upside of things,

10:32

right? How do we ensure that territories are balanced as much as possible? How

10:37

do we make

10:38

sure quotas are balanced? How do we make sure all of the key things that

10:41

operations revenue

10:43

operations focuses on is ensuring that there's a predictable way of achieving

10:47

numbers. That's

10:48

the piece to me that's important for CROs to really get deeper into and really

10:53

get a lot

10:54

more deeply engaged. And so I think as a CRO, if you're able to get into the

11:00

details and

11:01

the operating part of the role, I think it helps you really sort of set the

11:05

foundation

11:06

of how the entire revenue role executes its plan, right? So I think that level

11:10

of engagement

11:11

for a revenue leader is to me the difference that I notice in people really

11:15

understanding

11:16

the role and how to execute it.

11:18

All right, let's get to our first segment. Rev obstacles. We talk about the

11:21

tough parts

11:22

of RevOps. What are the key challenges that you think RevOps leaders are facing

11:26

right

11:26

now?

11:27

Yeah, I think one of them I highlighted, right? I think it's there are so many

11:30

different stakeholders

11:31

and it's really tough for a revenue operations leader when you've got so many

11:34

different customers,

11:36

right? So many different leaders that you've got aligning that to a care is

11:39

number one.

11:40

I think that's one of the biggest things. I think data is the other piece of it

11:43

, right?

11:44

We get data from a lot of different places and a lot of times you hear people

11:48

say, hey,

11:48

the data tells me this versus it's not that the data tells you, it's just how

11:52

you define

11:53

how you're looking at the data, the period of data you're looking at. So I

11:57

think that

11:57

piece of like looking at data and trying to make sense of what the data is

12:02

telling you,

12:03

it requires a lot of work. It requires a lot of analysis, a lot of work by the

12:07

teams that

12:08

capture the data and put that data together. So I think those two along with

12:12

just making

12:13

sure that you have a plan and a strategic plan that is achievable. I think that

12:20

's the hardest

12:20

thing, right? I think all of us as revenue leaders, I think there's a even with

12:24

a down

12:25

market and everything that's happening in macroeconomics, there is an

12:28

expectation and

12:29

rightfully that we drive revenue and we continue to maintain a high level of

12:34

growth in our

12:35

business. And I think obviously the revenue operations leader feels that just

12:39

as much

12:40

as the CRO does, I know my rev ops leader, we're always constantly thinking

12:44

about how

12:44

do we maintain this level of growth, right? And so I think that challenge that

12:49

you're

12:49

always faced with is how do you maintain growth? How do you make sure teams are

12:54

set up for

12:55

success? How do you have a predictable model around forecasting and all of that

12:59

? I think

13:00

those are the things that really make the job more challenging, but that comes

13:04

with

13:05

the territory. I think it's more of just that those are the things that myself

13:08

and my revenue

13:09

obsolete are constantly thinking about.

13:11

You talk a lot about like, okay, our isn't aligning objectives for sales,

13:14

marketing and

13:15

CS, like under revenue. I think that most companies are moving in that

13:19

direction and understanding

13:21

that those three functions, like how important they all are, especially if you

13:24

have like a

13:25

self-serve function and marketing owns a number or something like that. I'm

13:28

curious

13:29

like how you think about aligning objectives around seasonality as well,

13:32

because part of

13:33

the thing it seems like for those three different departments is end-of-quarter

13:38

obviously always

13:39

brutal for sales, end-of-year obviously always brutal for everybody, but

13:44

marketing a little

13:45

bit more flexibility there in terms of how they're running campaigns and how

13:49

you can

13:49

divert resources. Like at the end of the day, I think most rev-ops leaders are

13:53

like, I only

13:54

have so much time in bandwidth in the day. We have to triage and if it's always

13:59

sales

13:59

that wins or if it's always CS that wins or if it's always like new logo

14:03

creation that

14:04

wins, like other people do suffer and there's a little bit of a fixed pie there

14:07

. So curious

14:08

how you think about other ways to split the pie to make it more even and have

14:13

all three

14:14

functions get some attention.

14:15

Yeah. Look, I'm personally feeling that, right? I think for all the great

14:19

things that

14:19

we've done in aligning these different functions, I like to be deeply involved

14:23

in the business

14:24

and all aspects in both the marketing stuff, the sales, CS partnerships and for

14:30

someone

14:31

like me, I currently have 11 direct reports. These are all senior leaders in

14:35

the business

14:36

and just digging into each part of the business and making sure that we're

14:40

functioning and

14:41

we're aligned on what we're trying to go achieve. It's a tough task. I do think

14:44

like

14:45

anything else, I think having a strong leadership team that understands like

14:48

what they need

14:49

to go achieve in those functions is critical because you can't spread yourself

14:53

across

14:54

all of these things equally. So I think that's obviously a given that you have

14:58

to have a

14:59

really strong leadership. But I do think that the one area I personally have

15:03

really emphasized

15:04

on in the last couple of months that I've been here is really alignment between

15:10

myself

15:10

and our chief marketing officer and really just making sure that those two

15:14

functions

15:15

are completely aligned around what we're going to do because there's so much

15:19

stuff that we

15:20

do around sales and marketing both in our new business, partnerships and

15:26

customer success

15:27

that marketing gives us air cover, whether we're putting on events or whether

15:31

we're

15:32

putting on a dinner or we're doing broad based marketing campaigns or nurturing

15:36

. I think

15:37

that to me is extremely important. So sales leaders, the CS leaders, I think

15:42

those folks

15:42

are just making sure that the marketing function is tightly aligned. I haven't

15:46

been perfect

15:47

at it in my career and I think there's always been that friction between sales

15:50

and marketing

15:51

and I'm trying to break that. I'm trying to make sure that's a true partnership

15:55

for someone

15:56

like myself just to make sure that we're operating at the best possible way to

16:00

make sure that

16:01

the teams are aligned in that because marketing for all the challenges we have

16:05

on the sales

16:05

side, marketing is probably the one area that generally in the downturn they

16:10

get impacted

16:11

by and they get really questioned on, hey, what is the ROI on the spend? We're

16:15

going to

16:15

spend a million dollars. How do we ensure? And so marketing touches so many

16:19

things and

16:20

so we're constantly working with RevOps and just trying to make sure that we

16:24

can show

16:24

ROI and where marketing is impacting revenue, right? Both maybe directly or

16:29

indirectly and

16:30

the attribution and all of that. So that's a piece that really between myself,

16:34

our CMO

16:35

and our head of revenue operations, we're constantly trying to make sure that

16:39

we can talk to our

16:39

CFO and say, no, we are seeing impact in the outcomes of what marketing is

16:45

doing by the

16:45

following, right? I'll give you an example. I know one of the things we talked

16:48

about is

16:49

this is really tough for a lot of businesses, right? Because CFO is constantly

16:52

saying, hey,

16:53

how do I make sure I'm getting to return on this? And so we get into this

16:56

debate of attribution,

16:57

how does attribution? And last quarter, we had a fantastic quarter. We probably

17:02

had a dozen

17:03

very large deals ranging from 300,000 to three, four million dollars a year per

17:09

contract. And so

17:10

a lot of these customers came to our user conference event in September. And

17:14

every leader

17:15

spent time with these customers or prospects at the time, right? And so

17:21

marketing drove a lot of

17:22

that that put that customer over that decision to move forward with iterable,

17:27

with spending time

17:28

with the leadership team, with the various functional leaders, just to make

17:32

sure they felt good,

17:33

marketing drove a lot of that. So how do you attribute the cost of that event

17:37

to the impact

17:38

that it had in closing those deals? So that's a lot of the work that you

17:41

typically will do between

17:42

those key functions to make sure that you're able to back up the data.

17:46

It's a great story. And I think it speaks to the fact that the data will tell

17:50

you whatever you

17:51

want to hear. If you poke it hard enough and long enough, right? It's like, it

17:54

's going to tell

17:55

you what you want to hear. And I think that's the hard part when you're trying

17:58

to tie together sales

17:59

and marketing is there are so many the ghost stats that you don't see that you

18:04

're not measuring

18:05

that it's like, Hey, just for an example, it's like our outbound marketing,

18:09

like this works. We send

18:11

10,000 emails and we get drive X amount of business because 2% of people are

18:15

clicking on them and

18:16

whatever. That's yeah, but also 98% of people are just really annoyed by your

18:20

sales team that they

18:21

keep reaching out. So there are all these other things that have to be measured

18:24

where something

18:24

like a user conference where all those people are already in pipe, but that

18:28

pipe was now

18:29

actually closed. And it's influenced by this event, but it wasn't the final

18:34

thing that drove

18:35

them over the edge or was it? And that's where I think that a lot of rev ops

18:38

leaders, like you

18:39

have to look at that information and not be draconian and say like the event

18:44

caused all this stuff.

18:45

So no, but maybe it accelerated or maybe it's maybe we need to do smaller batch

18:50

events that

18:51

occur every month in different geographic like geographies to accelerate slower

18:56

deals or whatever

18:57

experiment test result sort of thing and not just make like sweeping general

19:00

izations. And I feel like

19:02

that is one of the big pitfalls of rev ops is to say, Hey, I think we found

19:06

something really

19:07

statistically significant and you take it to finance and they're like, Yep,

19:11

that's it.

19:12

Triple down here. And yeah, just say wait a second. That's not like the silver

19:17

bullet just because

19:17

this one function or this one thing was working quadruple down on just that

19:21

thing. It's no, we did

19:22

15 different plays. That was one of the plays that we can measure really easily

19:27

. But that wasn't

19:28

the entire reason. Yeah, no, I think you're spot on, right? Because I think

19:31

when you look at a

19:33

customer's buying journey and what they went through the people who came to

19:36

this event,

19:37

there was so much work we had done in acquiring that customer, getting them

19:42

into the pipeline,

19:43

getting them engaged. There's so many different parts of, yeah, no, obviously,

19:48

it's very easy

19:48

to look at the end result and say, this is what did it. But I think it's that

19:52

it's that influencing

19:54

fact that you try to figure out, yeah, look, I wish there was a silver bullet

19:57

that you could say,

19:59

this is the one thing and you can spend all your dollars here and you're going

20:02

to get that. But

20:03

that's not realistic. That's not how customers buy. That's not how customers

20:07

engage with you.

20:08

There's a variety of things, right? What marketing does on the website, what

20:12

they do in nurturing,

20:13

how we support current customers. We have a lot of customers who talk to their

20:18

peers and they say,

20:19

hey, what are you doing to engage yourself? And it's what we do in our customer

20:22

marketing side of

20:23

things and how we market what our customers do, like what I mentioned earlier

20:27

about how Dordash,

20:28

you use this like, Dordash is a great example. They talk to a lot of our

20:32

customers about,

20:33

here's what we do. And here's we run our entire platform on, on itable. And I

20:37

think that's also

20:38

a component. So yeah, I know it's really tough to just narrow down to one

20:41

little area and double click

20:43

while that would be great. It would be just a quick follow up question on the C

20:46

FO piece,

20:47

because I know that this is something that obviously every CRO faces and is a

20:50

difficult decision.

20:51

And part of the thing that is frustrating when you're talking to the CFO is

20:56

every second that

20:57

you're speaking to them, trying to justify all the stuff that you're doing. You

21:01

're not actually

21:01

working on all those things, but it's obviously a key part of the business to

21:05

be able to hit projections

21:06

and do all that stuff. And that's their job. But how do you find that balance

21:09

to say like,

21:10

hey, are we going to just spend every day trying to justify our existence? Or

21:14

can we just actually

21:15

go do the work? Yeah, no, I think, look, just like I mentioned at a business

21:19

level, you have to have

21:20

key metrics that you're tracking towards, right? That OKRs, whether it's here

21:24

or previously, I think

21:25

you've got to get aligned on what the revenue metrics is. Is it the magic

21:29

number? Is it the payback

21:30

period? Whatever that is, that you've got to get alignment with your CFO on,

21:34

you've got to work

21:35

towards that. That's the metric that you're tracking towards, right? If the

21:39

magic number is

21:40

what the CFO cares about and the CAC and obviously the payback, then everything

21:45

else is feeding into

21:46

that, right? So I think getting alignment on that is critical. And so that once

21:51

you get alignment on

21:52

that, and you both have agreed that, look, yes, ideally, we want to get to a

21:56

payback of this,

21:57

the following this year, sometimes it's your first year, you're investing in

22:01

maybe scaling a new

22:02

segment. And so the payback on that segment is going to be different, right?

22:05

You're going to go

22:06

into the enterprise segment and you're going to take a bet and your payback is

22:10

going to go from

22:11

from 12 months to 18 to 24 months because it's enterprise, you get alignment on

22:16

that with your

22:17

CFO while you still say, hey, our mid market business or SMB business to pay

22:22

back is 12 months,

22:24

and maybe we're going to try to get it down to 11 months. So I think those are

22:27

the things that

22:28

you want to know, it's like anything else, right? It's aligned around the key

22:31

metrics you want to

22:31

track, then agree on it, right? And then you track towards it and you're not

22:36

constantly debating

22:37

what the metrics should be. And so that to me is to me, the way that I found it

22:41

to be most productive

22:43

of working with my CFO. And so that's really what we've aligned on. Like,

22:48

easier said than done,

22:49

when you have a fantastic quarter and things are looking great, it's an easier

22:52

conversation.

22:53

When you have a rough quarter and you don't hit those things, it's a different

22:56

conversation,

22:57

but I think that's the world we all live in. And at the end of everything else

23:00

that you throw out,

23:01

it's all about execution, right? So a lot of times we spend time on what are

23:05

the leading

23:06

indicators that we need to focus on to make sure that we can hit the numbers

23:10

and the pipeline metrics,

23:12

the conversion rates, the enablement, a lot of things that we need to do for

23:16

the revenue teams

23:17

to make sure that happens. But that's really where I try to make my time and

23:21

the time we spend with

23:22

RevOps and the sales leaders. And we're going to get more into metrics here in

23:25

a second and our

23:26

next segment, the tool shed, where we're talking tools, spreadsheets metrics,

23:31

just like everyone's

23:32

favorite tool qualified, no B2B tool shed is complete without qualified. Go to

23:36

qualified.com

23:37

right now to learn more, check them out. We love qualified. They're the best.

23:42

Go to qualified.com

23:42

to learn more and fill out your tool shed. Bobby, let's talk about your tool

23:47

shed a little bit here.

23:48

Starting with metrics, what metrics matter to you, you talked a bunch about how

23:52

important they are.

23:53

Yeah, so I think there's a variety of things, right? I think when it comes to

23:56

the sales function,

23:58

we talk a lot about obviously what is our pipeline coverage by segment. I think

24:03

it's easy to say,

24:04

hey, we need to have 4x pipeline. But that's not always the case, right? So we

24:08

look at each segment

24:09

that we have, an interval, we have a SMB mid-market and enterprise segment. And

24:14

so obviously the pipeline

24:16

conversions and pipeline coverage are all different for those segments. We

24:20

spend a lot of time on

24:21

just figuring out what those metrics are. But it's around pipeline needed, how

24:26

much pipeline we need

24:27

to add on a weekly basis and to get our pipeline to a healthy state and then

24:30

obviously work on

24:31

the conversions. Conversions are, they can vary also in different segments in

24:35

the enterprise segment

24:37

for us. When you get into half a million into three, four million dollar deals,

24:40

the conversion rates

24:41

are different than $50,000 average deal size in our mid-market segment. So that

24:46

's primarily what

24:47

we focus on. And then on CS, we have different metrics. So those are the

24:50

primary ones that we look at

24:51

is around pipeline and conversions. Not to say that any leaders are tools here

24:57

in the tool shed

24:58

section, but I am curious that the key part of building a tool shed is choosing

25:01

a leader that's

25:01

going to manage it. I'm curious, like, how do you think about hiring a rev ops

25:05

leader? What do you

25:06

look for in a rev ops leader? What are the qualifications and the things that

25:10

you would say,

25:10

like that's someone who I want on the team? Yeah, I think for me, overall,

25:15

anyone I hire in the

25:16

organization, whether it's a revenue ops leader or sales leader, even an

25:21

individual contributor,

25:22

I generally look for people who have a growth mindset, right, who either have

25:27

been part of a

25:27

growth story before and they know what that feels like or just the way they run

25:32

their business,

25:33

they think about growth. And so I think that's number one, I think,

25:36

particularly for a revenue

25:37

ops leader, you want the person to be able to think what is possible, right?

25:42

Because when you're in

25:43

that role and you want to just look at data and say, data tells us we can only

25:47

grow at whatever

25:48

X. And I think you want that person that says, but why can't we go 10, 20%

25:54

higher? And so I think

25:55

growth mindset is obviously very important for me. Obviously somebody who can

26:00

roll up their sleeves

26:01

and really get into the data and not just only relies on their analyst to do a

26:05

lot of the work.

26:06

I think that's also very important. And then I really look for somebody who's

26:10

my, like I said,

26:11

who's my right hand person, it's my strategic counterpart that I can bounce a

26:15

lot of ideas off of.

26:17

And they can give me the data mindset, but they can also say, I think if we

26:21

stretch this, we can

26:22

have this type of outcome. So I think just that strategic partner that I can

26:27

lean on and have

26:28

candid conversations with have somebody who can push back on me and challenge

26:32

my thinking. I think

26:33

that's really somebody I look for in this role that I'm in right now, where I'm

26:38

only two months

26:38

and I have my ideas and I'm maybe naive about what's possible. So it's good for

26:43

somebody to

26:44

push back on me, but I do like that back and forth and help push the entire

26:48

organization towards

26:49

more of a growth mindset. Do you have any examples of something that happened

26:53

in the pipeline that

26:54

you noticed wasn't working that you fixed? I tell my team here, maybe it's a

26:59

bit of a control freak,

27:00

and I'd like to get into the details and mask and a lot of questions. Okay, why

27:04

is it like that?

27:04

Why did we do this? I think sometimes when you build models and you're building

27:09

a revenue model

27:11

and you're building the growth model, right, and saying, hey, we need X amount

27:15

of opportunities,

27:16

we need X amount of conversion, and you have those key metrics around how much

27:20

pipeline needed,

27:20

what your conversion rates are. And you don't look deep enough. And hey, how

27:25

many accounts are we

27:26

assigning to the team? And how many accounts are we focused on on a monthly and

27:30

quarterly basis?

27:31

Sometimes the math doesn't add up. And so that's the piece to me, at least as a

27:36

CRO,

27:36

I like to be deeply involved in a lot of those details to make sure that I

27:40

understand it

27:42

and what we're doing makes sense. One, because 20 years, it's been a long time,

27:46

but 20, 22 years ago, I was a sales rep. So my thinking always goes back to how

27:51

do we make

27:52

these salespeople successful, right? What do they need to do? Of course, we're

27:55

going to push

27:56

and we're going to push them to do more than they think it's possible for them

28:00

to do. And so

28:02

we're going to do that. And I tell my team that all the time, you've got to

28:04

lean in, you've got to

28:06

be an entrepreneur, you've got to know your territory, you've got to know your

28:09

accounts,

28:10

we're going to push you. I want to make sure the logic, the math makes sense of

28:13

like,

28:13

how many accounts we're giving you, what the conversion rate is and all of that

28:17

. So that's

28:18

the piece to me that I've sort of sometimes noticed is we make decisions

28:21

without necessarily

28:22

going deep enough into it. And I think it's very common for leaders in a

28:27

business to

28:28

speak from a very high level and say, we're going to do this and this. And so

28:32

to me, that piece of

28:33

it, it's not one thing. I know you asked what's the one thing I caught in the

28:36

pipeline or in the

28:37

business. It's more of just a level of detail to make sure the conversion rate

28:42

and the math makes

28:43

sense that it's rooted in some realistic outcome, right that you need to have.

28:48

Yeah. And how to take action, it's to the point earlier with user conference,

28:52

it's like, hey,

28:52

this thing went really well. We saw a bunch of these big deals close. This was

28:56

clearly

28:56

something that influenced pipeline. Now what? Okay, what does this mean we're

29:01

going to do more of

29:01

these? Does this mean we're going to make next year's bigger? Do we need to do

29:04

satellites? Do we

29:04

need to do is it was at the in person aspect of it? Was it just that we'd never

29:08

got on a plane and

29:09

met any of these people? And this was the first time because of COVID or

29:12

something like, it's just

29:13

like all those secondary effects of like, why was this impactful and what is

29:18

our thesis? And then

29:19

how can we take actions that accelerate the things that are working and what

29:24

the data is telling us

29:25

and then testing or if you do one of these next time and it doesn't work? Well,

29:30

it's like, oh,

29:31

I wonder why that is, et cetera. It's drawing a direct correlation into some of

29:36

these things.

29:37

It's harder, right? It's harder. We've even done things where we've gone back

29:40

and studied and

29:41

asked customers, hey, how did you engage with us? Why did you engage? And a lot

29:46

of that, it's not

29:47

like, oh, you sent me this email and that's what did it? No, it rarely is that,

29:50

right? It's our

29:51

people in a buying cycle. Are they not in a buying cycle? Sometimes you're not

29:56

in a buying cycle,

29:57

but you're so frustrated with the solution you have that is breaking and it's

30:01

causing impact

30:03

that you finally make a decision. And so it's really hard to draw one specific

30:07

things. I think

30:08

the best that we try to do is to understand what are the most common things

30:12

that happen and really

30:13

focus on the few and try to make the best decisions possible based on the few

30:19

examples that we see.

30:20

That's a hard piece of the job is figuring out where you should really invest

30:23

your dollars and

30:24

your focus. Any blind spots that you feel like you wish you could measure

30:28

better?

30:29

Yeah, I think I came from Freshworks, which is in the sort of sales cloud,

30:34

service cloud space,

30:36

right? Solutions that customer service organizations run and then at Interpol

30:40

now,

30:41

which we work with a lot of marketers about how they communicate with our

30:44

customers. And so

30:45

a lot of companies already have solutions, right? And we're going after a mid

30:50

market or an enterprise

30:51

size company. They're not buying a marketing automation solution for the first

30:55

time. They've had

30:56

solutions. And so the blind spot a lot of time, obviously we believe we have

31:00

the most modern,

31:02

powerful platform that's built on all the new technology stack versus the

31:06

legacy players.

31:08

But understanding the blind spot probably for me would be when is the buying

31:13

cycle, right?

31:14

When is the right time that we should be speaking to this customer? If there

31:18

was tool sets out there

31:19

and there are tools out there that tell you they're running this legacy system

31:23

and they're on a

31:24

contract for another two, three years, that doesn't mean that you prevent

31:28

selling into that customer.

31:29

There's ways you can work with that customer in its new department or new

31:33

product division and

31:34

get a land deal in that. But I think that's the piece that's really if you're

31:38

selling a solution

31:39

that is replacing an old platform, the blind spots are when and how and where

31:45

in the company you can

31:46

get a footprint into that company to use your platform. That's the piece

31:51

probably that we still

31:52

try to fine tune of in your total addressable market. Where should you go focus

31:58

as the highest

31:59

likely to convert? And that's probably the part that we really spend a lot of

32:03

time on,

32:04

which we still don't have a clear path to right now. All right, let's get to

32:08

our final segment here.

32:10

We're just going to do some quick hits quick questions if the answers quick

32:14

hits popular.

32:14

Yes, I am. Number one, what advice would you have for someone who is newly

32:20

leading rev ops or go to

32:21

market team? Listen and learn if you're doing it for the first time. Just

32:26

observe and learn.

32:27

Don't be quick to just make decisions. Do you have a favorite book or podcast

32:31

or TV show that

32:32

you've been checking out recently that you enjoy? No, maybe I'll pick this one

32:35

up.

32:36

Listen to some rise rev ops. I like it. It's great. A lot of good nuggets. If

32:41

you were an animal,

32:42

what animal would you be? Oh, wow. Okay. Something in the ocean, maybe a

32:48

dolphin or something.

32:49

Just I'm always been very intrigued by the depth of the ocean and what's

32:53

possible because

32:54

obviously a place that many of us have not gone. And that's, yeah, I would say,

32:58

a dolphin. Maybe

32:59

a shark. I like it. Anything to plug? It's been awesome for listeners. They can

33:03

go to iterable.com

33:05

to learn more. We'll link it up in the show notes. Any final thoughts for our

33:08

audience here?

33:09

No, I guess the one thing I'd say you probably have a lot of practitioners, a

33:12

lot of revenue

33:13

ops, practitioners and leaders. I guess what I would say is you guys have a

33:17

critical role in the

33:18

business, probably at least from a CRO's perspective, probably the most

33:22

critical role.

33:23

And just being a business partner for not only the CRO, but the rest of the

33:28

organization

33:29

is something that I think is instrumental into a company's success. Being

33:33

aligned around the

33:34

business schools of the company, I think that is a great place to be for a

33:39

practitioner in revenue

33:41

operations. Just partner, challenge yourself, challenge your own thinking. The

33:45

data doesn't

33:46

always give you everything. I think there's some in-sensual things that you

33:50

need to focus on.

33:52

But I think that's the piece I'd say continue to be a great partner for the CRO

33:55

and other

33:56

leaders in the organization. Bobby, it's been awesome having you on the show.

34:00

Thanks so much. I'm going to talk to you. Great. Thanks, Ian.

34:11

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