Outbound Prospecting Best Practices: Daniil Krets of Esper.io

We’ve had the privilege of working with some of the most cutting-edge and accomplished SDR leaders in SaaS over the last year. These leaders and their teams at fast-growing companies like Esper, Carrot Fertility, Amperity, iSpot, and more have helped shape the Relevvo product. Here’s the next post in our series where we share some of these gathered outbound prospecting insights with you.

Daniil Krets of Esper.io

We’re thrilled to welcome Daniil Krets, Senior Manager, Global Sales Development at Esper. Esper is an Android DevOps platform for dedicated, mission-critical devices that allows the engineering and operations teams to have full control over the full lifecycles of hardware and software applications.

Daniil has spent the last 6 years building a career in sales development prospecting the Marketing, Customer Education/ L&D, HR/Benefits, and senior business decision-maker functions. Most recently, Daniil has scaled a global SDR team from 4 to 17, and built out inbound and outbound functions in NA and APAC regions.

Esper has partnered with Relevvo over the last year to help improve its SDR effectiveness and efficiency. We were thrilled to get a chance to sit down with Daniil to get his thoughts on prospecting, team management, and what most companies get wrong in their quest to build a productive outbounding engine.

Aashish Dhamdhere (AD): Daniil, thanks for joining us, what is the top piece of advice that you would give to someone that’s trying to establish an outbound prospecting program?

Thanks for having me! I think of targeting and conversation quality as a 2×2 matrix. If you think about it, the ideal situation is when you get the targeting and the conversation quality right. That hits the sweet spot. These are also the two dimensions of learning. You’re trying to get the targeting and the quality of conversations right in the early days. My learning is that you can make progress even with sub-par conversations if you get the targeting right. That’s something that I encourage every SDR Manager to keep in mind as they establish an outbound prospecting program. 

In the early days of establishing an outbound prospecting program, you’re going to have a lot of bad conversations. But if you get the targeting right from the beginning, chances are that even with bad conversations you’re going to learn a lot faster and be much more successful later. This way you can focus on nailing the conversations and on aligning the conversations with your value prop and the audience’s needs.

An important thing is that the danger zone in the 2×2 is where you’re having good conversations with the wrong target audience. This shows up as meetings that are not leading to opportunities and deals. Watch out for this!

AD: That’s great advice, Daniil. You mentioned learning and the importance of learning, especially in the first 6-months. How do you ensure that the team is learning well?

Learning is important all the time, but it’s most important in the first 6-months of a new outbound program. I feel really fortunate that here at Esper, I’ve been given the freedom to experiment and learn. The early-stage journey is really difficult, especially if you’re trying to build a category where you serve a broad audience with a variety of use cases. It helps tremendously if you work at a company where there’s an existing culture of experimentation. We have that here at Esper!

If in the first six months, you’re focused only on achieving results and not on learning, the odds are high that you’re not going to make it a year. This is because you hit your goals only if you learn and adapt quickly.

The important thing is that to learn, you have to have a process, and the process needs to be based on measuring the things that matter. The other thing is that you have to celebrate learning as much as you celebrate meeting goals. Learning should be treated as a first-class goal and it should be tied to progress metrics!

Of course, outcome metrics like meetings booked and opportunities generated matter. You also have to look at the response and connect rates, the quality of conversations in tools like Gong or Avoma, and how well you’re doing in addressing objections. It helps to collect and share these learnings, not just within the team, but also with your stakeholders in Marketing and the rest of the Sales organization.

AD: Love that! If you think about your SDR and your SDR Management journey, what is the most counterintuitive or non-intuitive thing that you’ve learned about prospecting in your SDR management journey?

Let me start by sharing what I’ve learned from an SDR Management perspective. There’s a ton of advice out there about prospecting and SDR Management, especially on places like LinkedIn. There’s advice about cold calling, content, sequences, timing, about email length. You have to be very careful in evaluating this advice before you decide to adopt it. 

Most of this advice is well-meaning, but it’s based on that person’s experience in a particular industry, with a particular audience, with their product and price point, and at a given time. In the early days, I wouldn’t just take this advice and try to apply it. I learned that you have to take a critical eye and figure out the portion that applies to you and forget the rest. This is the tricky part! 

I’ve seen some SDR Managers move industries and try to apply the same playbook that they’ve used with HR in the past now with IT or a different function, and that just doesn’t work. Then SDR Managers get frustrated or they’re gone in 6-months. Don’t do this! Always remember that when you move industries or products, you will have to spend the first few months learning! Or at the very least don’t assume that what’s worked in the past will work again.

The other thing to remember is that even if the advice is from someone in your industry, the advice still does not work 100% of the time. It’s all about taking this advice and figuring out how you can apply it creatively. And about testing and measuring. As early as possible, form a baseline of your response rates, then you can apply this advice and see what’s working and what’s not.

AD: You mentioned the importance of focusing on learning. How do you get the team and your stakeholders to buy into this approach and your philosophy?

Two different approaches here based on if you’re managing up or down. When you’re managing up and to your peers, you want to manage with data. You build trust with data with your peers and your managers. 

When you’re building a new outbound program, you want to analyze the pipeline generated, analyze the meetings booked closely, break it down, identify the patterns that are working, and then do more of what’s working. You share what you’re learning widely and regularly. You share data not just to give visibility but also to get input into what you’re testing. This sharing of data is what builds trust with your stakeholders. 

When it comes to getting buy-in from SDRs, you have to start with the understanding that in many companies SDRs are perceived as second-class citizens. There’s this assumption that you don’t need to get their buy-in. This is so wrong. You have to get the team bought into the “why” before you talk to them about the “what” and the “how”. Spend 15-minutes sharing this context. Do it a few times! 

Something you have to do in addition to this is to show the team that it can be done. That you can book meetings and generate a sales pipeline using the strategy that you’ve mapped out. So one of the things that I’ve done at Esper is that I often run prospects through the sequences that I’ve put together and book some meetings. This helps build trust in the approach and the strategy. I also often ask my SDRs whenever they’ve reached a point where they’ve tried everything they could with an account or a prospect if they would like my help in seeing if they will respond to me. I find that this lands much better than asking the generic “What can I do to help?” question.

You also have to remember that different things motivate different people, and so when you’re trying to motivate SDRs, keep this in mind. There is no one size fits all approach that works!

AD: There seems to be a metrics framework that you’re following here to earn trust with your Management team and your SDR Team. Can you please share more?

The best way to build trust is by measuring and sharing your business impact, and that’s pipeline and revenue. These metrics are particularly important because companies have to invest a lot in tools, enablement, and compensation to have effective SDR teams, and they have to know that they’re getting a positive ROI for those investments.

We have a performance-based culture, and here the trust that you’ve built and your internal brand will be measured by business impact. This is something that I did not initially recognize as an SDR, but also something that I now go out of my way to help the SDRs understand and internalize.

There are a few things that are hard to measure but very important to track and share. The speed and extent of your experimentation, as an example, and how quickly you can pivot based on the lessons learned. How well you’re supporting Marketing in driving Inbound numbers. And how quickly you’re able to build a quality team that’s delivering results. All these things help build trust.

For the team, we measure activity, connect rates, response rates, and conversion rates to meetings booked and opportunities generated. I feel this is a pretty standard set of metrics today with outbounding in the industry. What you want to do here is establish a baseline as early as possible so that then when you’re learning and applying your lessons learned, you can see the impact on these operational metrics. Then, you can share this trend with the team, and even at the individual SDR level so they can see progress.

AD: One last question for you, how are we at Relevvo helping the team at Esper improve their outbound efficiency and effectiveness?

In your first question above, we talked about the importance of targeting in getting an Outbound program going and in then scaling that program. That’s where Relevvo has been most impactful for us. It is an important foundational piece on which we’ve built our outbound program, and we’ve seen some amazing success in Q1 with Relevvo.

You’ve helped us double the number of accounts that we can process in a given week with the MDR team. You’ve helped us take a more sophisticated approach to our targeting, and our persona-based messaging, and together these things have helped us exceed our Q1 meeting and pipeline numbers. We’re also getting great feedback from the AEs on the quality of meetings booked, and our meeting-to-opportunity conversion rate is north of 70%!

Relevvo has been tremendously helpful, and I also feel like we’re only just beginning this journey with you in terms of everything that I see as possible. I feel like we are no longer limited in terms of putting our targeting and segmentation ideas to work, and that’s exciting! 

AD: Thanks a ton, Daniil! We really appreciate you taking the time to share your hard-earned insights with us. We hope to have you back on at some point in the future with a new set of questions!