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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.
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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:
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:
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.
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?](https://assets-global.website-files.com/61c9fe00acd90d5e82f7014d/645127df9d843264a5a9066e_0d56b963.png)
Here’s everything we use:
Our single source of truth for everything. And where we see all our meetings booked through Chili Piper
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.
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
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
So our SDRs can book meetings on behalf of AEs while they're on the phone or right from an email
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
“All the answers are in Guru. Please look it up in Guru and ask a friend before asking me.”
Did my demo run? How’d the meeting go? Watch the Gong.
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
For making GIFs
To determine tools a prospect uses on their website. So far most accurate when it comes to our prospects tech stack
To determine our prospects’ web traffic.
We collaborate super closely across our entire company — including partnerships, marketing, AEs, and between reps and managers.
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.
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.
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.
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].](https://assets-global.website-files.com/61c9fe00acd90d5e82f7014d/64512b247b09182b410468da_Slack%20Shout%20Out%202%20(1).png)
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.
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.
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:
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:
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.
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:
Here’s everything we use:
Our single source of truth for everything. And where we see all our meetings booked through Chili Piper
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.
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
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
So our SDRs can book meetings on behalf of AEs while they're on the phone or right from an email
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
“All the answers are in Guru. Please look it up in Guru and ask a friend before asking me.”
Did my demo run? How’d the meeting go? Watch the Gong.
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
For making GIFs
To determine tools a prospect uses on their website. So far most accurate when it comes to our prospects tech stack
To determine our prospects’ web traffic.
We collaborate super closely across our entire company — including partnerships, marketing, AEs, and between reps and managers.
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.
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.
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.
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.
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.
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.
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 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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