How 17 SDRs Booked 580 Meetings in Q1

Joey Williams
May 2, 2023
min to read

You know those cold emails you get? 

Well, I’m the person who leads the team that sends the best of those in the world. 

The ones that make you think “wow — how did they possibly send something so relevant, so clever, so smart?” 

Since you are such a generous, thoughtful person who goes out of your way to compliment our SDRs, I’ll let you in on a little secret.

How 17 SDRs Booked 580 Meetings in Q1

Joey Williams
May 4, 2023
min to read

You know those cold emails you get? 

Well, I’m the person who leads the team that sends the best of those in the world. 

The ones that make you think “wow — how did they possibly send something so relevant, so clever, so smart?” 

Since you are such a generous, thoughtful person who goes out of your way to compliment our SDRs, I’ll let you in on a little secret.

We send some bad ones too… 

Like - *get your name wrong and say you work for a different company* bad. 

We learn from those. And we appreciate you not yelling at our reps who are brave enough to make mistakes on their way to learning and success. 

Along the way, we level up as world-class salespeople and we seek to provide more value to our prospects — and convert more of them into customers.

Want to know how it’s going?

Closed-Won in Q1 was ridiculous. 

We achieved 172% of our goal for SDR-sourced Closed-Won $. We did that by hitting 102% of our goal for Qualified Meetings Held. 

Over the last two quarters, we converted 40% more Closed-Won ARR per dollar of pipeline than the year before. We’ve gotten more efficient at booking quality meetings with happy prospects that turn into happier customers. 

Let’s get into how:

1. We built a repeatable and scalable daily process for our SDRs

Having a daily process is essential for our reps’ success. But it’s not a one-and-done system. We continue to evolve and adapt it, maintaining the best process for our team.

To find those relevant prospects, we use a free tool called Magical Text Expander — this gives our SDRs the boolean searches they need to populate the best fits on SalesNav.

To make sure we’re working each account and prospect efficiently, we have daily standards of follow-up on email, LinkedIn, and cold-calling. The daily baseline is:

  • 200 emails
  • 30 calls
  • 15 LinkedIn messages. 

Based on what’s working for our top reps and across the industry, these numbers adjust over time to ensure we’re not wasting any activities. Across a team of 17 reps, each inefficiency is costly. 

To ensure our process continues to improve, we lean on each other (managers and SDRs) as well as other teams across Chili Piper. And we also lean on our Coaching Checklist to make sure nothing slips through the cracks over time.

2. We have a message that resonates

Our early SDRs worked hard to create and prove the success of relevant messaging that resonated with our ICP. 

One example of this is taking a quick screenshot of our prospects’ Request a Demo Form and tailoring the message to how we could help qualify, route, and book their inbound leads

By making our messaging about our prospects, we found a repeatable way to be relevant to them and stick out against the hundreds of cold-email they receive per week. 

Here’s an example of one of our highest-performing emails: 

Hey [first name] - Is there a reason why you're not letting the 51K website visitors you get monthly book a meeting directly through your book a demo form? It looks like the state and company name fields are helping your sales team to qualify + route potential customers in your CRM. Other security companies like [competitor name] are increasing inbound conversions by 60-80% by qualifying and booking their leads right from the form. I have ideas on how you can also do this, especially given your sales team is pretty big and has grown by 1% this past year. You must have some inbound-hungry reps right now! Open to learning more?

3. We have an awesome tech stack 

Here’s everything we use: 

Salesforce

Our single source of truth for everything. And where we see all our meetings booked through Chili Piper

Meetings Booked

Also, our Sales Ops Wizard, Phil, changed the color of our interface last year to make it a slightly darker shade of blue - game changer. 

SalesLoft

Best place for refreshing the URL constantly to see how many times your prospects open your emails while not responding

We also use Salesloft to automate our cadences for no-shows, webinar leads distribution, and pretty much any other email we have to send out

Sales Engagement

LeadIQ

The answer to “how on earth did you get my number?” - sorry, Chris. 

We also get our emails from our LinkedIn Navigator research from LeadIQ

Contact Data

Chili Piper

So our SDRs can book meetings on behalf of AEs while they're on the phone or right from an email

Book meetings for your sales team in one click

Chili Piper automatically routes to the next AE in the round-robin queue, which means our reps don’t need to scramble through a spreadsheet to find the right rep. 

Our SDRs have very simple qualification criteria they get from prospects to know that they are a technical fit for our products. Once they get that, they use Handoff to book directly to correct AE in one click. As soon as it's booked, an opportunity is automatically created in Salesforce, with the AE and SDR tagged as owners, and then the SDR adds the notes of what the prospected is interested in, their qualification info, and anything else helpful to make the call go smoothly.

Once the prospect shows up to the meeting, it is marked as a Qualified Opportunity by our AE and the SDR automatically received their Qualified Held Meeting credit.This creates a smooth transition into our sales pipeline, a simple criteria for SDRs to follow, and  easy tracking

Guru

“All the answers are in Guru. Please look it up in Guru and ask a friend before asking me.” 

Knowledge Management

Gong

Did my demo run? How’d the meeting go? Watch the Gong.

Projection Central

AKA the best damn forecasting tool in the world.

Shoutout Projection Central aka P-Cent, a spreadsheet we made utilizing the magic of G-Connect, Z-scores, and Love

Cleanshot 

For making GIFs

GIFs

Wappalyzer

To determine tools a prospect uses on their website. So far most accurate when it comes to our prospects tech stack

Wappalyzer

SEOQuake 

To determine our prospects’ web traffic.

SeoQuake

4. We like each other  

We collaborate super closely across our entire company — including partnerships, marketing, AEs, and between reps and managers. 

Slack message alert for a new booked meeting, for SDR Annabelle Jones. Everyone on the SDR team commented in the Slack thread, congratulating Annabelle for a new booked meeting.

Partnerships 

By working with our Partnerships team, we’ve created specific cadences we send to customers of our partners, highlighting how Chili Piper works with their current tech stack to advance their Inbound Conversion process. 

These have proven to be extremely successful, converting over 2X from Account Worked→Opportunity Created compared to our typical outreach. 

Marketing  

Across SaaS, SDR teams are moving more to sit under marketing instead of sales. While our SDR team is firmly part of the Sales Org, we work closely with our marketing team to ensure we’re not missing opportunities. 

Our marketing and sales leadership teams have weekly meetings to discuss what messaging is working in our ads and cadences, and we find creative ways to convert marketing engagement into Sales Opportunities. We focus on the outcome first and attribution second. 

AE team 

As I mentioned, our SDRs are firmly part of our SDR org. Like our AE team, we comp them on a percentage of closed-won dollars they source (in addition to commission for Opportunities Created alone). As such, we have a two-way feedback loop between our SDRs and AEs. 

Slack shoutout: 10% of our SDR pipeline for the month has been sourced by @Aaron Wallace in the past 3 days alone. Unbelievable. Shoutout @Travis Warden and all the other AEs moving these monster dears along. 33 clap reactions, 19 star eye reactions, 6 rocket ship reactions

Along with a leadership team who values our reps’ input, we make sure we’re continuing to improve our joint processes and working toward one goal. 

Slack message: S/O to @Amina B for this fire call! She is so natural, creates great rapport, uses mirroring brilliantly, asks amazing questions, snags the qualification q's at the end of the call like a champ! About to have this demo and I'm so pumped to chat with [blank].

SDRs and leadership 

One of the most important feedback loops is that between our SDRs and our SDR Leadership. In order for SDRs to focus on what they can control, they have to trust that the roadblocks they can’t control are being actively addressed by leadership (like fixing bugs in tools, improving our cadence messaging with data, etc.).

Most of our Monday training come from feedback our SDRs provide on what they need support with. Additionally, each new top performer on our team brings their own spin to the role and new best practices we can take away. While our leadership team allocates time and resources to scaling these takeaways, our reps take on leadership roles as well when they see something working. 

OK guys - I’ve been through 6 from the 31 meetings booked by king  @Dale O’Shea , There is two ways we can look at the performance : => Quantity : I’m unfortunately not able to have numbers - but what we all know is that he is volume beast - Phone + Emails - Remind me  @Dale O’Shea  Are you having the same 24 H a day like all we have :joy::joy: ? => Question : How to do the same :disguised_face::disguised_face::disguised_face: => Quality : :hot_pepper: First : Dale is soooo knowledgable about Chili Piper - Especially Concierge and Handoff - Having no difficulty switching from a Concierge use case to a Handoff or Instant booker pitch - on the phone and on email - Impressive !! :hot_pepper: Then, if I chose 2 things that he is a superstar at : Objection Handling :exploding_head: :exploding_head: and Phone call confidence :phone::phone: Objection Handling : Example, Look at this example from this call He got 3 objections : Objection 1: My team is reaching back immediately after an inbound comes in => Great ! - Typically companies see that people for some reason don’t answer.

In the example above, you can see one of our previous high performing SDRs, Amina, sharing her own takeaways from the success of a (then) new rep, Dale. This is a shining example of how our reps do their own research into what’s working and push our leadership team to spread what’s working across the team. 

Every meeting booked by our team is met with enthusiastic celebration from the rest of the team. Each meeting is an opportunity to learn — as well as an opportunity to lift up your teammates.

Wrapping up

At Chili Piper, we keep experimenting until something works. Then, we tell the world about it. 

If you want to hear about the other things we’re doing in marketing and sales, follow along on LinkedIn — or subscribe to The Sauce, the spiciest newsletter in B2B. 🌶️

We send some bad ones too… 

Like - *get your name wrong and say you work for a different company* bad. 

We learn from those. And we appreciate you not yelling at our reps who are brave enough to make mistakes on their way to learning and success. 

Along the way, we level up as world-class salespeople and we seek to provide more value to our prospects — and convert more of them into customers.

Want to know how it’s going?

Closed-Won in Q1 was ridiculous. 

We achieved 172% of our goal for SDR-sourced Closed-Won $. We did that by hitting 102% of our goal for Qualified Meetings Held. 

Over the last two quarters, we converted 40% more Closed-Won ARR per dollar of pipeline than the year before. We’ve gotten more efficient at booking quality meetings with happy prospects that turn into happier customers. 

Let’s get into how:

1. We built a repeatable and scalable daily process for our SDRs

Having a daily process is essential for our reps’ success. But it’s not a one-and-done system. We continue to evolve and adapt it, maintaining the best process for our team.

To find those relevant prospects, we use a free tool called Magical Text Expander — this gives our SDRs the boolean searches they need to populate the best fits on SalesNav.

To make sure we’re working each account and prospect efficiently, we have daily standards of follow-up on email, LinkedIn, and cold-calling. The daily baseline is:

  • 200 emails
  • 30 calls
  • 15 LinkedIn messages. 

Based on what’s working for our top reps and across the industry, these numbers adjust over time to ensure we’re not wasting any activities. Across a team of 17 reps, each inefficiency is costly. 

To ensure our process continues to improve, we lean on each other (managers and SDRs) as well as other teams across Chili Piper. And we also lean on our Coaching Checklist to make sure nothing slips through the cracks over time.

2. We have a message that resonates

Our early SDRs worked hard to create and prove the success of relevant messaging that resonated with our ICP. 

One example of this is taking a quick screenshot of our prospects’ Request a Demo Form and tailoring the message to how we could help qualify, route, and book their inbound leads

By making our messaging about our prospects, we found a repeatable way to be relevant to them and stick out against the hundreds of cold-email they receive per week. 

Here’s an example of one of our highest-performing emails: 

Hey [first name] - Is there a reason why you're not letting the 51K website visitors you get monthly book a meeting directly through your book a demo form? It looks like the state and company name fields are helping your sales team to qualify + route potential customers in your CRM. Other security companies like [competitor name] are increasing inbound conversions by 60-80% by qualifying and booking their leads right from the form. I have ideas on how you can also do this, especially given your sales team is pretty big and has grown by 1% this past year. You must have some inbound-hungry reps right now! Open to learning more?

3. We have an awesome tech stack 

Here’s everything we use: 

Salesforce

Our single source of truth for everything. And where we see all our meetings booked through Chili Piper

Meetings Booked

Also, our Sales Ops Wizard, Phil, changed the color of our interface last year to make it a slightly darker shade of blue - game changer. 

SalesLoft

Best place for refreshing the URL constantly to see how many times your prospects open your emails while not responding

We also use Salesloft to automate our cadences for no-shows, webinar leads distribution, and pretty much any other email we have to send out

Sales Engagement

LeadIQ

The answer to “how on earth did you get my number?” - sorry, Chris. 

We also get our emails from our LinkedIn Navigator research from LeadIQ

Contact Data

Chili Piper

So our SDRs can book meetings on behalf of AEs while they're on the phone or right from an email

Book meetings for your sales team in one click

Chili Piper automatically routes to the next AE in the round-robin queue, which means our reps don’t need to scramble through a spreadsheet to find the right rep. 

Our SDRs have very simple qualification criteria they get from prospects to know that they are a technical fit for our products. Once they get that, they use Handoff to book directly to correct AE in one click. As soon as it's booked, an opportunity is automatically created in Salesforce, with the AE and SDR tagged as owners, and then the SDR adds the notes of what the prospected is interested in, their qualification info, and anything else helpful to make the call go smoothly.

Once the prospect shows up to the meeting, it is marked as a Qualified Opportunity by our AE and the SDR automatically received their Qualified Held Meeting credit.This creates a smooth transition into our sales pipeline, a simple criteria for SDRs to follow, and  easy tracking

Guru

“All the answers are in Guru. Please look it up in Guru and ask a friend before asking me.” 

Knowledge Management

Gong

Did my demo run? How’d the meeting go? Watch the Gong.

Projection Central

AKA the best damn forecasting tool in the world.

Shoutout Projection Central aka P-Cent, a spreadsheet we made utilizing the magic of G-Connect, Z-scores, and Love

Cleanshot 

For making GIFs

GIFs

Wappalyzer

To determine tools a prospect uses on their website. So far most accurate when it comes to our prospects tech stack

Wappalyzer

SEOQuake 

To determine our prospects’ web traffic.

SeoQuake

4. We like each other  

We collaborate super closely across our entire company — including partnerships, marketing, AEs, and between reps and managers. 

Slack message alert for a new booked meeting, for SDR Annabelle Jones. Everyone on the SDR team commented in the Slack thread, congratulating Annabelle for a new booked meeting.

Partnerships 

By working with our Partnerships team, we’ve created specific cadences we send to customers of our partners, highlighting how Chili Piper works with their current tech stack to advance their Inbound Conversion process. 

These have proven to be extremely successful, converting over 2X from Account Worked→Opportunity Created compared to our typical outreach. 

Marketing  

Across SaaS, SDR teams are moving more to sit under marketing instead of sales. While our SDR team is firmly part of the Sales Org, we work closely with our marketing team to ensure we’re not missing opportunities. 

Our marketing and sales leadership teams have weekly meetings to discuss what messaging is working in our ads and cadences, and we find creative ways to convert marketing engagement into Sales Opportunities. We focus on the outcome first and attribution second. 

AE team 

As I mentioned, our SDRs are firmly part of our SDR org. Like our AE team, we comp them on a percentage of closed-won dollars they source (in addition to commission for Opportunities Created alone). As such, we have a two-way feedback loop between our SDRs and AEs. 

Slack shoutout: 10% of our SDR pipeline for the month has been sourced by @Aaron Wallace in the past 3 days alone. Unbelievable. Shoutout @Travis Warden and all the other AEs moving these monster dears along. 33 clap reactions, 19 star eye reactions, 6 rocket ship reactions

Along with a leadership team who values our reps’ input, we make sure we’re continuing to improve our joint processes and working toward one goal. 

Slack message: S/O to @Amina B for this fire call! She is so natural, creates great rapport, uses mirroring brilliantly, asks amazing questions, snags the qualification q's at the end of the call like a champ! About to have this demo and I'm so pumped to chat with [blank].

SDRs and leadership 

One of the most important feedback loops is that between our SDRs and our SDR Leadership. In order for SDRs to focus on what they can control, they have to trust that the roadblocks they can’t control are being actively addressed by leadership (like fixing bugs in tools, improving our cadence messaging with data, etc.).

Most of our Monday training come from feedback our SDRs provide on what they need support with. Additionally, each new top performer on our team brings their own spin to the role and new best practices we can take away. While our leadership team allocates time and resources to scaling these takeaways, our reps take on leadership roles as well when they see something working. 

OK guys - I’ve been through 6 from the 31 meetings booked by king  @Dale O’Shea , There is two ways we can look at the performance : => Quantity : I’m unfortunately not able to have numbers - but what we all know is that he is volume beast - Phone + Emails - Remind me  @Dale O’Shea  Are you having the same 24 H a day like all we have :joy::joy: ? => Question : How to do the same :disguised_face::disguised_face::disguised_face: => Quality : :hot_pepper: First : Dale is soooo knowledgable about Chili Piper - Especially Concierge and Handoff - Having no difficulty switching from a Concierge use case to a Handoff or Instant booker pitch - on the phone and on email - Impressive !! :hot_pepper: Then, if I chose 2 things that he is a superstar at : Objection Handling :exploding_head: :exploding_head: and Phone call confidence :phone::phone: Objection Handling : Example, Look at this example from this call He got 3 objections : Objection 1: My team is reaching back immediately after an inbound comes in => Great ! - Typically companies see that people for some reason don’t answer.

In the example above, you can see one of our previous high performing SDRs, Amina, sharing her own takeaways from the success of a (then) new rep, Dale. This is a shining example of how our reps do their own research into what’s working and push our leadership team to spread what’s working across the team. 

Every meeting booked by our team is met with enthusiastic celebration from the rest of the team. Each meeting is an opportunity to learn — as well as an opportunity to lift up your teammates.

Wrapping up

At Chili Piper, we keep experimenting until something works. Then, we tell the world about it. 

If you want to hear about the other things we’re doing in marketing and sales, follow along on LinkedIn — or subscribe to The Sauce, the spiciest newsletter in B2B. 🌶️

Joey Williams

Joey Williams is the Director of Sales Development at Chili Piper, overseeing our outbound motion. Outside of work, he makes music and does not run marathons (or anything like that).

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