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The effectiveness of outbound sales is declining.
Buyers are self-educating. They rely on their peers to discover new tools. They reach out directly to someone with a similar title and ask questions around how they’ve handled role specific challenges.
All of this has led to outbound conversion rates dropping rapidly.
73% of SDRs aren’t hitting quota (Operatix and Pavillion).
66% of AEs hit quota in 2022 (Bridge Group AE Metrics 2023).
Becc Holland, Founder and CEO Flip the Script has advised and consulted 100s of the top SaaS companies and reinvented their outbound strategy. She's taken companies that average a less than 1% response rate and got them to 20%+.
Part of what Becc teaches her clients is a framework around educating and informing your target audience around problems that they didn’t know existed.
And Becc is breaking down her framework so you can achieve greater response rates with your outbound program.
How to Craft an Outbound Strategy Leading with Unknown Problems is broken down into 3 key sections:
By the end of this article, you will understand the problems that plague outbound, and how to craft a strong outbound playbook by understanding your buyer and the unknown problems they may be unaware of.
And/or check out our full interview with Becc Holland:
In order to improve your outbound program, we first need to understand what are the current flaws in how companies are doing outbound sales today.
The main point around what is wrong in outbound sales today is that many companies lead with addressing known pains or problems.
“Typically people like you tend to struggle with ________, do any of these resonate?”
“Are you running into this problem?”
“Are you in the market for ____?”
You are targeting a small subset of buyers that are:
a) in buy now mode OR
b) are experiencing the problem that you are leading with.
However, if the problem was large and painful enough they would have already been looking for a solution. So most outbound strategies now are designed to target a fraction of your total addressable market simply by leading with problems that are known to your buyers.
According to Becc:
Pain = anything that’s a negative experience in the present moment
Problem = anything that you solve for
All pains aren’t problems. Not everything that is annoying, you’re not going to solve for. And not all problems are painful. But sometimes you’re trying to solve to avoid pain in the future.
"Salespeople have the opportunity specifically with an outbound, but just across the funnel, to understand are there any current impacts they didn't know about, future impacts they didn't know about, problems that they didn't know about, root causes they didn't know about." - Becc Holland
What is the main task of any sales rep?
It’s not learning the latest sales techniques, or understanding how to handle objections.
According to Becc, the purpose of sales is to diagnose. And if you don’t know your buyer's world, you aren’t able to diagnose.
"If you're in sales, your expertise is to diagnose. If you don't have that, you have no expertise." - Becc Holland
By leading with problems that are unknown to your buyer and understanding the metrics that drive your buyers decision making, sales reps can create a sense of urgency and mobilize buyers to take action. Ultimately increasing the effectiveness of your outbound sales program and driving more pipeline and revenue for the business.
A problem for your buyer: something that prevents them from getting to their main metrics & KPIs (key performance indicators) or prevents them from achieving a goal in relation to the metric.
So let’s reverse engineer this. Let’s say your buyer is a Director of Demand Gen for a B2B SaaS company.
Sample ChatGPT prompts:
Based on these prompts, you can start to have an understanding that things like:
are key metrics for our Demand Gen Buyer Persona and are top of mind when making any decision.
The last prompt lets us understand that cross functional collaboration with sales, product and CS is key and can limit the impact of any demand generation program.
An over emphasis on short term goals and not thinking of long term strategy is also another reason why many Director’s of Demand Gen don’t end up getting promoted.
"The quickest way to earn credibility, rapport, and get a sale out of thin air is to identify for them the problem they didn't know they had." - Becc Holland
Becc’s framework consists of 5 steps:
Here is what that might look like when we take the buyer persona for Chili Piper, a Director of Demand Generation:
The only way for your message to resonate with the majority of your target audience is to educate them. To show that you understand their world and their problems. A problem for your buyer is something that prevents them from getting to their main metrics & KPIs or prevents them from achieving a goal in relation to the metric.
To recap:
The effectiveness of outbound sales is declining.
Buyers are self-educating. They rely on their peers to discover new tools. They reach out directly to someone with a similar title and ask questions around how they’ve handled role specific challenges.
All of this has led to outbound conversion rates dropping rapidly.
73% of SDRs aren’t hitting quota (Operatix and Pavillion).
66% of AEs hit quota in 2022 (Bridge Group AE Metrics 2023).
Becc Holland, Founder and CEO Flip the Script has advised and consulted 100s of the top SaaS companies and reinvented their outbound strategy. She's taken companies that average a less than 1% response rate and got them to 20%+.
Part of what Becc teaches her clients is a framework around educating and informing your target audience around problems that they didn’t know existed.
And Becc is breaking down her framework so you can achieve greater response rates with your outbound program.
How to Craft an Outbound Strategy Leading with Unknown Problems is broken down into 3 key sections:
By the end of this article, you will understand the problems that plague outbound, and how to craft a strong outbound playbook by understanding your buyer and the unknown problems they may be unaware of.
And/or check out our full interview with Becc Holland:
In order to improve your outbound program, we first need to understand what are the current flaws in how companies are doing outbound sales today.
The main point around what is wrong in outbound sales today is that many companies lead with addressing known pains or problems.
“Typically people like you tend to struggle with ________, do any of these resonate?”
“Are you running into this problem?”
“Are you in the market for ____?”
You are targeting a small subset of buyers that are:
a) in buy now mode OR
b) are experiencing the problem that you are leading with.
However, if the problem was large and painful enough they would have already been looking for a solution. So most outbound strategies now are designed to target a fraction of your total addressable market simply by leading with problems that are known to your buyers.
According to Becc:
Pain = anything that’s a negative experience in the present moment
Problem = anything that you solve for
All pains aren’t problems. Not everything that is annoying, you’re not going to solve for. And not all problems are painful. But sometimes you’re trying to solve to avoid pain in the future.
"Salespeople have the opportunity specifically with an outbound, but just across the funnel, to understand are there any current impacts they didn't know about, future impacts they didn't know about, problems that they didn't know about, root causes they didn't know about." - Becc Holland
What is the main task of any sales rep?
It’s not learning the latest sales techniques, or understanding how to handle objections.
According to Becc, the purpose of sales is to diagnose. And if you don’t know your buyer's world, you aren’t able to diagnose.
"If you're in sales, your expertise is to diagnose. If you don't have that, you have no expertise." - Becc Holland
By leading with problems that are unknown to your buyer and understanding the metrics that drive your buyers decision making, sales reps can create a sense of urgency and mobilize buyers to take action. Ultimately increasing the effectiveness of your outbound sales program and driving more pipeline and revenue for the business.
A problem for your buyer: something that prevents them from getting to their main metrics & KPIs (key performance indicators) or prevents them from achieving a goal in relation to the metric.
So let’s reverse engineer this. Let’s say your buyer is a Director of Demand Gen for a B2B SaaS company.
Sample ChatGPT prompts:
Based on these prompts, you can start to have an understanding that things like:
are key metrics for our Demand Gen Buyer Persona and are top of mind when making any decision.
The last prompt lets us understand that cross functional collaboration with sales, product and CS is key and can limit the impact of any demand generation program.
An over emphasis on short term goals and not thinking of long term strategy is also another reason why many Director’s of Demand Gen don’t end up getting promoted.
"The quickest way to earn credibility, rapport, and get a sale out of thin air is to identify for them the problem they didn't know they had." - Becc Holland
Becc’s framework consists of 5 steps:
Here is what that might look like when we take the buyer persona for Chili Piper, a Director of Demand Generation:
The only way for your message to resonate with the majority of your target audience is to educate them. To show that you understand their world and their problems. A problem for your buyer is something that prevents them from getting to their main metrics & KPIs or prevents them from achieving a goal in relation to the metric.
To recap:
Arthur Castillo currently heads Dark Social & Enangelism at Chili Piper, where he recently transitioned as one of the top performing Account Executives. He brings a unique view to marketing with his 7+ years in sales and is on a mission to blur the lines between sales and marketing. Based in Toronto, Canada, in his spare time you can catch him watching NFL or soccer, playing fantasy football, and looking to improve his chess game! Connect with Arthur on LinkedIn.
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