Sales development has become a mission critical element in just about every high growth sales & marketing organization. When run well, the SDR function adds speed, efficiency, and standardization to the sales process.

In anticipation of the TOPO Sales Summit, LeadGenius sat down with Andrew Berger, Head of Sales Development at Square, for a special Q&A preview of his upcoming talk on SDR development at TOPO.

In the past two years, Andrew has scaled Square’s SDR team while also building out a new enterprise team to focus on high growth accounts.

In this post, Andrew offers insight into how SDR leaders can set their teams up for success.


sales development at square


Sales development has rapidly become a mission critical element in just about every high growth sales & marketing organization today. Why is this the case?

Andrew Berger, Head of Sales Development at Square

[Andrew Berger] The sales development function has become so valuable for both sales and marketing teams for two reasons.

First, it enables high-growth companies to quickly iterate and test while they scale. Trial and error have always been a part of the sales process, but the SDR role specifically allows sales teams to learn quickly from messaging and targeting strategies in the wild. A sales leader can prove a concept, such as exploring a new vertical, before spending a ton of money on it.

Second, the sales development function enables a company to do more with less. From an organizational perspective, it makes sense to have highly specialized roles with specific targets and goals. From a training and career perspective, it is more efficient to teach a young SDR to do a specific and fundamental function of the sales very well before moving on to their next role. A well-run sales development team sets its reps up for long-term success in the organization.


In what ways does the strategic role of the SDR contribute to the overall business objectives of a company like Square?

I think the real value of the SDR function comes back to testing. SDRs are on the ground floor validating and powering a business’ go-to-market strategy. If we decide to drive a new type of customer, service a different market segment, or launch a new product, the SDRs play a key role.

We have a team of highly trained and skilled people to proactively reach out to our ideal accounts with email messaging and phone calls. An organized blitz by the SDRs enables us to see if the message resonates or not.

When we have a new product offering to launch, we work with lead generation partners to source the right kinds of account and contacts. Our SDRs know very quickly if our messaging and targeting is correct. This is a very effective way to validate product market fit.

We used this approach when we launched our first retail point of sale application. We immediately saw traction at the top of the funnel and knew that our messaging and outreach was on target. We also had a clear path to further improve and scale our strategy.


You know what it’s like to build a sales development team from the ground up. What are some ways SDR leaders can be proactive when setting their teams up for sustainable growth?

SDR leaders must be very forward-thinking.

You first need to work with leadership to understand the company’s core objectives. Once you know where the business wants to go, you can work backward from there.

Start with an idea of realistic conversion rates, win rates, multiples, revenue, and profit. Set benchmarks for each metric.

If things do not work as you suspected, systematically examine where there is a breakdown. What part of the funnel is not working? Is it the activity types? Is it something as simple as subject lines messaging? Is training insufficient? Are the personas off?

Isolate what is not performing well and go fix that. Start at the beginning.

[Tweet “”The real value of the SDR function comes back to testing…” @ae_berger @square”]


When moving upmarket, how do you prioritize personalization, volume, and efficiency? What role does personalization play in your team’s sales development process?

Balancing personalization, volume, and efficiency is a challenge for every SDR team. The answer depends on the team.

We use a pseudo account-based strategy at scale. Like many teams, when we first started out, it was largely spray and pray. That yielded some results. However, through experimentation, we realized that when decreased the amount of leads per rep, we actually saw in increase in conversion rates? Why? Personalization.

Personalization should be something very relatable or relevant to the business. As you move up market, this becomes even more important. SDRs need to be strategic with their personalization.

I’ll give you a real example. One of my reps recently contacted a large retail business with multiple locations. A few days before, the business was written up in the New York Times. By referencing a quote by the decision maker that was included in the article, our rep was ultimately able to get that decision maker on the phone. That personal touch made the difference.

Personalization really is key.

You start with a template. That is the base layer, but then you do something like a 3×30: take thirty seconds to learn and reference three unique facts about the business. For some sales processes its three minutes; for other its 30 minutes. It depends on the audience and the sales team. Crafting a story is vitally important.

We allocate time for lead and account generation. We also allocate time for personalization that overlays our pre-built templates so that we’re not really starting from scratch every time. The more we can automate the process, the better.


What are the most significant ways the function of inbound lead qualification differs from predictable outbound lead generation at the rep level?

For our teams, inbound lead qualification and outbound prospecting are vastly different roles.

At Square, reps that come in and do inbound lead qualification are zero to 48 months out of school. It’s their first job. They learn Square; Salesforce; no bad habits. It’s a lot of repetition and immersion in sales culture and the sales floor to understand what it takes to be successful. We want every rep to understand our company’s core mission. Square’s goal is economic empowerment. These reps are not on variable commission. We want them to focus on learning.

In the outbound role, it’s honestly vastly different. We work with partners who deliver us highly-targeted leads and we do sourcing on our own. There’s always work to be done. Outbound sales development is the first entrance to variable sales at Square. Reps have the opportunity make what they want out of the role.

As you move up through the ranks from sales development to closing, you get fed inbound and outbound opportunities from different sales development teams.


You’ve been working with LeadGenius for over 2 years now. How has LeadGenius helped inform your go-market-strategy?

LeadGenius is a very helpful partner for us.

With LeadGenius, we are able to iterate on our targeting strategies quickly. We went from spray and pray, to a more personalized, account-based approach at scale. Sales development is all about being able to identify the correct ICPs and getting the right volume of contacts. LeadGenius has helped us define our best audience segments has helped us with our go-to-market strategy. There’s no question about it.


You will be speaking TOPO Summit. What will you be talking about at topo?

My talk at TOPO Sales Summit will be centered around how to build a world-class sales development org. There are three different tenets I am going to speak about.

First, predictable and repeatable growth. Second, understanding sales’ influence on the overarching business organization. And third, career progression.

I’ll be giving attendees an inside look into what worked well for us at Square. I’m looking forward to seeing everyone there!

LeadGenius helps companies like Square test and capture new verticals.

Schedule a Demo of LeadGenius Today.