How to turn SDRs into great AEs with Datadog's Neil Flanagan

About the expert Neil Flanagan: 

Neil is a top SDR leader at Datadog, where he's been for the past 5 years, and helped to scale the SDR team. Currently he owns the midmarket and enterprise SDR team, leading a team of 6 SDR managers who each have ~7 SDRs on their team.

One of the most impressive parts of Neil's approach to leadership is his ability to get his team promoted from SDR to successful AE. He walked us through how he approaches skill development.

What are the skills that SDRs need to be promoted?

“At the end of the day, you wanna sell a solution that's gonna help someone accomplish their goal and get to where they wanna go. You need to understand, again, the industry and why they are looking at digital to be able to answer "How does Datadog provide value to those to those industries, to those challenges".  If we can get the SDRs to understand why that matters, we can get them to have a really good discussion.

What does an SDR need to make this a reality? 

Softskills:

• Networking 
• Executive presence
• Self-Sufficiency 
• Organization

Tactical Skills

1. Account planning is a major lever in teaching people how to understand a business, and what motivates them. 
2. Cold calls 
3. Good discovery we use Command of the Message (check out how force management uses Champify). Goals are to identify the companies ideal state and current pains
4. Objection handling

What are the time horizons for rep development?

A promotion requires a rep be ready at the time headcount is available, but the Neil built his SDR program where his SDRs are generally ready to promote around ~14 months. He focuses on different milestones across development to ensure a rep is not only a great SDR, but is ready for the next horizon.

Weeks 1-2: Onboarding

This is classic company onboarding - getting access to tools, company overview, etc. 

Months 1- 3: Become a self-sufficient SDR

Once onboarded to the company, reps learn the ropes of the role - how to be an SDR. The goal is to make reps independently successful so they don’t need the weekly managers. At the end of three months reps are expected to have an organized routine and operating rhythm for:

• Prospecting
• Account research
• Outbound activities (cold calls, emails, etc.) 
• Setting meetings
• Converting meetings
• The SDR -> AE hand off

Months 3-9: Become the BEST SDR

Once they have a good handle on the basic skills, the coaching is tailored on an individual basis based on KPIs and the data. What does that mean? Neil and his managers look at different KPIs and have conversations with the AE team where each team member needs to strengthen their skill set. They look at activity metrics and conversion metrics across each stage of the funnel. 

As the SDR’s skills improve, they encourage our SDRs to work more closely with the AEs on account plans which expands

Months 9+: Develop AE skills 

Start to introduce the ability to demo and  command of the message (our sales methodology and framework). This includes coaching on:

1. Mini demo certification
2. Analyzing discovery calls
3. Aligning outbound and meetings with sales methodology 

“If you do this right a rep is no longer just going after a meeting to book a meeting, but they start to dig into pain and qualify calls beforehand. That is what the AE mentality shift is like so when they’re an AE they know how to set 14 high quality engagements a month that are going to lead to next steps, not just educational calls”

How and what do you measure to track SDR progress?

Activity KPIs

‍The metrics we track a day are a 100 KPIs a day roughly 60/40 split between calls and emails. 

Conversion KPIs

Our benchmarks are roughly 6% of calls should convert into conversations, and about 25% of conversations should turn into a meeting.

Meeting KPIs

With about 60 dials, that's about 5 combos a day. That's about one meeting a day.

Tying it all together

When managing you have to apply two lens:

1. Manage to results, don't pay attention and enforce activity metrics for the activity.
2. Tailor the coaching and activity expectations for each rep based on their metrics

When Neil looks at metrics he's asking: How many meetings are you generating a day? How many meetings are you generating a week? Are those meetings that you're generating being captured? Are they converting into actual quota bearing activities for you?

The goal of an SDR being self sufficient is that they can determine what they need to do in order to be successful.

I want SDRs to outpace the conversion ratios. I want someone to come to me and say, "hey, I only have to do 90 activities a day because I have a 7% connect rate and because I'm booking at a 30% rate."

You can go at your own pace as you are hitting your numbers, we're getting the results, I'm fine with that. If you start to, you know, slip a little bit, we're back up to a 100, but that's just the way that I kind of have managed it.

What is your operational rhythm? 

Organizing your calendar is one of the most important skills for an SDR. One approach is have a 2 week process, where you focus on account planning for my next accounts the first two weeks + reaching out to my researched accounts 

“When you're first starting as an SDR in month 1, it's the most hectic. But if you do a good job with this, then you've got your current accounts that you're working, and you've got your future accounts that you know you're gonna be, switching targets to or switching attention to.

And those are the ones that you start to build out 2 weeks ahead, 30 minutes a day contributing to this. As you then start to work the accounts, this is a living document.”

How do you train your reps to build an account plan?

Step 1: Train your team on research

There are two types of research your SDR needs

1. Company research: 10-ks, investor pages, 3rd party articles, linkedin: why does the company do what what they do , how do they make money and how are they using digital applications to generate money (this is because datadog is in the observability market), and what key risks are they facing, and what internal information has our team already gathered. 
2. Industry research: what are major trends in the industry looking at forrester, gartner, accenture, etc. 

Step 2: Use research to build a Point of View (POV)

These two things combine to form a hypothesis. Determine a way to answer the question:

“This company is making money x y z, and this industry is growing this way. How can we kinda think about where this company might be a laggard or where they might be trying to advance their application development or their observability strategy?” 

Step 3: Use research and recent events to build proof points

Take your research and use it to nurture and provide ongoing value. "You see a news article from 3 months ago, you're in a conversation with someone, that's an awesome thing to bring up on a conversation, on a cold call, or in an email. " The ultimate goal is you are building yourself a one pager about the companies goals and initiatives, especially as you have more conversations. If done right, you have all the tools you need to have a targeted conversation about strategy.

How do you get SDRs to learn from AEs?

Help your SDRS prep for their 1:1s with their AEs - that’s the best place to level up, and prepare. Coming prepared to these 1:1 conversations to learn on the job, what an AE is thinking about, creates a conversation that helps SDRs learn “deal thinking” and be better prepared to hone on aspects of accounts that makes them more likely to close at the end of the day. SDRs need to:

Summarize their learnings from calls and make sure they are on the same page and getting the same takeaways as their AEs

1. This is what i’m hearing about the pain people are experience
2. These are the trends I’m hearing
3. These are the deals i’m excited about and why

“ that open dialogue is absolutely critical for good AE/SDR partnerships. It’s what's gonna allow you then to make sure you're not having misses or frustrating an AE by setting up meetings that they're not expecting that the quality or you're off the target.”

Come prepared with an account strategy 

As an SDR you shouldn’t just blindly do what an AE says. Come to the meeting with a proposed strategy whether that’s an article that makes you think an account is a good time or a hypothesis on how you attack an account. Use this to get feedback from the AE, and iterate and learn. 

At the end of the day you need to understand why an AE wants to target certain accounts. 

To wrap things up:  Hot takes on SDR promotion paths

 What’s the biggest misconception SDRs have about being an AE?

“I  think the biggest challenge for that I see with SDRs I promote is they come back to me about 6 months in the role and they go, I didn't know I still had to be an SDR. And I'm like, yeah, that thing doesn't go away. You still are doing all the SDR work. You're still doing all the PG.”

What is the biggest challenge/skill set gap? 

“I think the biggest gap though that I see is is basically discovery and and negotiation skill set. I think that's something that a lot of SDRs don't have exposure to. Even if we do a good job with discovery role play training here at Datadog, there's still so many scenarios  that we might not cover.”

What is the pro tip for SDR’s to level up on discovery/negotiation in advance? 

If you're curious on how to do that, talk to your AEs, pick their brains. If you get a good meeting, ask them how it's going. Follow that. Keep an eye on it. When it comes to final stages, how are you overcoming objections or challenges? How are you making sure that that goes? Even just getting that slight exposure is super beneficial at the SDR role.

Want more of Neil's advice? 

Check out the full video and get the resources here.