Sean Lane Revenue Leader
Revenue Leader Interview

Ops and the Changing Expectations of B2B Buyers with Sean Lane of Drift

Consumer expectations in the world of B2C buying have changed considerably in the last decade. However, especially in light of the pandemic, those same expectations have seeped even further into the B2B buying cycle.

In this fascinating interview, Sean Lane, Director of Operations at Drift, discusses his insights into how Ops can help facilitate GTM teams’ shift to optimizing this new buying journey.

Below are excerpts from that conversation that have been lightly edited for clarity.


Hey Sean, thank you so much for taking the time to chat with us today.

Sean Lane:

Thanks for having me, happy to be here.


Let’s start with a bit about you. Could you tell us about your background and your journey to the operations space as well as what you are doing today at Drift?


I started my career learning entrepreneurship through a fellowship program called Venture for America. It was only 40 of us in that first class, which was an amazing experience. I really didn’t know anything about entrepreneurship or startups before finding Venture for America.

The more I learned about it, the more I was attracted to that idea of going to a smaller company and being able to make an impact really early.

And learning a ton.

The whole idea behind VFA was sending recent graduates to startups. Not in the New York, Boston, or San Francisco’s of the world; it was in places like Providence Rhode Island, Detroit, New Orleans, and Cleveland.

That was how I got my intro into this world.

I ended up at a Providence-based startup called Swipely, which later became Upserve, and stayed for five and a half years.

The best part about my time there was being able to work across a whole bunch of different parts of the customer journey. I spent my first three years in post-sales doing things like onboarding, account management, support and ended up running those teams.

I then made a complete jump to the other end of the customer journey to running our SDR team, which gave me my first exposure to the sales process. That experience gave me the best learning ground for Ops. Being an SDR manager means you have to figure out the Ops side of things when it comes to reporting, funnels, and conversion rates.

That exposure helped me identify a need that, as we were growing, we had these silos popping up. I noticed that we needed a way to look across the entire customer journey and because of my experiences up to that point, I was uniquely positioned to do that.

We ended up starting a centralized Ops team in my last year that I was there.

That was the foundation for me in terms of learning the ropes of working in Ops.

I was able to take that experience and leverage it into my time at Drift.

For the last three years at Drift, I’ve been working across all the different parts of the customer journey. But, most specifically, from an Ops perspective – Sales Ops, Marketing Ops, CS Ops, and more recently really focusing on the sales part of that.

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In your experience, where does Ops fit in the overall GTM strategy?


Since the beginning, we’ve made a conscious effort at Drift to make Operations a strategic partner to all of the different Go-to-Market motions as opposed to a support function.

Everyone says it’s a nice thing for Ops to have a seat at the table and to be a strategic partner, but it’s a significant amount of work to make that a reality.

I think that by being a strategic partner and setting up that relationship really early, we were able to build trust over time with leaders across all of those functions.

You have to continually earn and prove that trust to keep the strategic partnership alive. I think us focusing on that at Drift has allowed the team to really grow. We partner really closely with each of those GTM teams on everything from planning processes to the execution of how their world works, as well as all the reporting that goes along with that.


What do you see as the greatest challenges you see on a day-to-day basis in creating that strategic partnership?


The most important thing is to stay on the same page with those leaders about what the priorities are. We have particular routines and cadences with each of those leaders to make sure that we do.

There’s a balance there though. You have to be nimble enough to change when priorities change, but you also have to be disciplined in a way that keeps teams on track.

For example, every Monday afternoon our Sales Ops team meets with our CRO and all of our Sales VPs to review the current top priorities and how we are doing against our goals. In addition, we look at if there are any new priorities that have come up that might need to be bumped to the top of the list, which then might bump something else down.

Having that constant flow of communication to make sure that Sales Ops priorities are aligned with Sales priorities – those should be the same thing.

Making sure that my team is aligned with the Sales leadership is the most important part of that relationship.


It seems like the focus on making sure silos don’t develop between GTM teams is an important one for you, how can GTM teams stay aligned and avoid this kind of “silo syndrome“?


Certainly, some of the routines I just mentioned are part of that.

But I also think that people get really caught up on what the perfect org structure is for an Ops team in order to be able to reduce those silos. I’ve worked in a number of different structures from an Ops perspective and found it’s much less about the specific structure and more about the approach that you bring to it.

From an org structure perspective, I’ve seen two main functions that have emerged as popular within Ops:

  1. Centralized Ops Model: I think of this as a hub and spoke model in which you have Ops at the center and all these different spokes that go out to your GTM teams. But, ultimately, Ops is the thing you can come back to in the middle.
  2. Decentralized Model: This is more function-specific with Sales Ops being directly aligned with sales, Marketing Ops is directly aligned with marketing, and so on.

But, as I said, I think it’s more about how you approach the work that you are doing more than who you report to.

The tendency if you have a problem right in front of your face is to smack that problem away. That’s usually what people do, but what happens in Ops is when you smack that problem away, there’s usually a ripple effect on other parts of the business from the decision you just made.

What we try to focus on at Drift is to better understand what the impact on other teams would be from any change we make.

Being able to take a step back and understand the ripple effects of any decision is the most important thing and outweighs any org structure decisions.


What are the changes you have seen COVID-19 have on the GTM team’s work and what kinds of challenges has that posed for Revenue Operations leaders?


First of all, a lot has changed – almost everything.

I think the biggest thing that has changed is the process by which there has been this shift from the companies having all the power and dictating the terms to the buyers having all the power.

That shift was already happening, but it has just been massively accelerated based on the pandemic and all the people working from home.

What we talk a lot about at Drift is that we are trying to remove friction from the buying process and what the pandemic has done is basically accelerate that process to the point where everybody has the same expectations in a B2B buying motion that they would in their own B2C life.

If you or I were to order DoorDash for dinner, buy something on Amazon, or order an Uber, we want it to be fast, convenient, and on our terms.

When I go to work, I don’t become B2B Sean – we still have the exact same expectations.

So I think what we are seeing is those expectations creeping into the B2B buying process.

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From a company perspective at Drift, we hope that our product helps people to do that. But from an Ops perspective, as you look under the hood of that buying process, you have to make sure you have the instrumentation, systems, and plumbing in place to facilitate that.

It sounds nice when you say “let’s get this website visitor to the right person at the right time in their buying process,” but how you think about designing that buying process is the part where your Ops team comes in.

We spend a lot of time instrumenting our systems to be able to do that to be able to connect the buyer with the right person at the right time.

It’s one thing to acknowledge that expectations have changed, it’s another to instrument your GTM and buying and selling processes to fit all of those changes.


Do you see those changes persisting? What are some things that Ops teams can do to best meet those needs?


Yes, I think it’s here to stay.

The concept of taking a client or a prospect to a steak dinner and having enterprise reps flying all over the country is going to diminish greatly.

That’s one behavioral shift that I think is going to continue.

In addition, we’re very strong proponents of the idea that AI is going to play a significant role in this process when it comes to meeting buyers where they are at and on their terms any time of day.

Our belief is that AI is not necessarily going to replace all interactions, it’s going to do the things that humans don’t want to do anyway and make the process more efficient for both the buyers and the sellers.

From an Ops perspective, you have to figure out how AI can be incorporated into the buying process in a way that still feels authentic and makes sure you are still leveraging humans for the thing that humans are doing best – creativity, building rapport, etc.

Whether you are in sales, CS, or marketing, you have to figure out what that balance is.

It’s not going to be either/or – it’s both.


What are some low-hanging fruits that GTM teams can apply today to deal with those shifts in B2B buyer expectations?


The place that I always start is looking at the hand-offs.

Anywhere where you have hand-offs inside of your customer journey, you have a possibility for inefficiency.

When leads are getting distributed from a marketing organization to an SDR team, there’s a ton of levers to make that conversion better. If you are talking about handing off from an SDR team to a sales organization, there’s a ton of hand-offs and potential inefficiencies there.

The same thing applies when you have a new customer come on board that needs to be passed to a post-sales team.

Each one of those places, to me, is always the place where I start to look for the inefficiencies and how to root them out.

I also think it’s important to note for Ops people that when I talk about the customer journey, you have two sets of customers as an operator.

You have the internal customers, which are the members of the GTM team that you are partnering with.

And then you have your actual customers.

So when I talk about finding ways to make the customer journey more efficient, I’m equally talking about both groups. I think if you ignore one or the other then you are doing that group a disservice. 

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