Improve 2024 Challenger sales bottom line with task automation

Last Updated on 
March 19, 2024
Automating Boring Work
Automating Boring Work

It’s 2024. You love using Challenger sales tactics to close deals and connect with prospects. The sales model brought to life by Matthew Dixon and Brant Adamson in their 3-part book series.

But how can you make the Challenger approach smoother? Just ride the wave of new workflow automation software. It’s a recipe designed to help sellers save time prospecting and customizing outreach.


We’ll connect you with tools to improve Challenger workflows (or any other sales strategy you follow).

Automate the Challenger sales process

Challenger walks sales reps through 5 steps. Each designed to help sellers redirect the conversation and keep focus on the few core details that matter most. Let’s automate them.

Challenger selling framework: 5 steps to closing

Step 1: Warm ‘em up

Initiate contact with prospects to uncover their goals and business challenges. Let’s speed this part up.

Sellers can automate the research process with OpenAI and summarize text from any open page. How much time can this save you?

Step 2: Reframe the problem for them

Challenge pushback from clients. Offer them new insights that combat their concerns and support your offerings. Generate summary and action items from meeting notes to expedite this step:

Step 3A: Rational drowning

Shower prospects with a plethora of data-driven evidence. This is to highlight how important it is you fix their problem. To breeze past this, sellers can extract data from any website using AI data analysis tools.

Step 3B: Create emotional impact

Speak to the customer’s heart through efficient storytelling and personalized messaging. Use generative AI to draft their emails and refine this workflow in a flash. Try it!

Step 4: Forge a new way

Open up a dialogue with your customer. Embrace 1:1 time with prospects to work on intuitive solutions together. Let’s simplify this.

Pairing with Slack can automatically send messages or trigger specific tasks. That goes a long way. 

Step 5: Present your solution

This step brings all the background research and preparation together. It’s the seller's last chance to convince the prospect their solution will improve their problems. 

Want help with this? Bring ChatGPT into the mix. Integrate OpenAI into your workflow and you can help them: 

  • Brainstorm unique ideas
  • Translate languages
  • Generate content

5 types of sellers & favorite automations

It’s crucial to understand the 5 types of sellers. Many B2B sales reps have at least one of these profiles. 

Recognizing this granularity empowers team members to capitalize on each person's strengths and weaknesses. It's about matching the right seller with the right prospect for maximum impact. 

And that’s not all. 

Each seller works differently, so understanding the sales automation they thrive using is crucial!  

The hard worker

Mostly known for their relentless work ethic and dedication. These sellers excel in staying motivated. Just imagine how automated personal productivity can skyrocket their results.

Do you resonate with this seller type? Then you could benefit from task management and productivity automation to help stay organized. Just download Bardeen and get started for free.

The relationship builder

They’re driven by forging strong connections and trust with clients. Relationship builders are best at building rapport and effortlessly becoming a part of anyone’s inner circle. 

If the relationship builder type sounds like you, we can help! What if you could qualify leads from LinkedIn faster? Speed up the sales cycle by automating the boring research with this automation:

The lone wolf

Independent and self-reliant, the lone wolf thrives in autonomy and individual achievement. 

Realizing you may be more of a lone wolf? You might benefit from boosted efficiency. Try using this email automation for outreach and follow-ups.

The problem solver

This seller persona is highly analytical and solution oriented. Problem solvers have a knack for pinpointing customer challenges and uncovering how to fix them. 

Are you a problem solver? Then you’ll want to channel the power of data analysis by using predictive analytics to get things done.

The challenger

Bold and assertive, this seller pushes back, or challenges a customer's assumptions. They’re great at:

  • Fueling constructive debates
  • Steering the conversation
  • Inspiring the prospect to take action
  • Inspiring other sellers to take action

Do you resonate with the Challenger? Customize your own workflow with ChatGPT-style AI for automation. Type what you want to automate in the box and Bardeen will build a workflow for you.

The Three Ts

Sellers that fit into The Challenger archetype demonstrate three crucial capabilities. Also referred to as ‘The Three Ts’, these sellers can exceptionally:

  • Teach prospects by collecting and sharing relevant insights at the right time.
  • Tailor the sales message effectively by gathering crucial data points on the prospect. 
  • Take control of the sale by assertively guiding the customer from pitch to close.

How do you stand?

Only 17% of B2B buyer’s time is spent meeting with potential suppliers. Just think about that. This is a newsflash to sellers: invest more time in your prospects. But how to free up some of that precious bandwidth in the first place? Make more time. Target redundant processes with automation.

Let’s visualize it together. Just imagine how much time you’d save with AI sales automation! You’d shorten the path to conversions and close more deals than before. 

Challenger sales methodology - coaching sellers into Challengers

How to coach sellers into Challengers

The Challenger seller persona isn’t something you’re just born with. It’s something you learn about and improve through consistent learning and perhaps some guidance. Fortunately, there are a lot of resources available to expedite this

Organizational resources and support go a long way towards transforming sellers into the Challengers of tomorrow. 

Want to turn your team into Challenger sellers? Managers can use a direct approach by coaching the individual seller personas. To be effective, each persona will need specific guidance.

Coaching a hard worker

The hard worker will go all in on Challenger training. Consistent coaching goes a long way with them. Make sure you give detailed feedback on their development in routine 1:1s. 

Expect to spend time organizing feedback meetings. Integrate Google Meet into the workflow! It’s a video conferencing app perfect for sharing presentations with teammates directly from your browser.

Coaching a relationship builder

Redirect them from focusing too much on building relationships. Instead, they can switch gears and tailor their client outreach with market research automation. Focusing on how to anticipate customer challenges or rebuttals when the time comes.

Want a tip? Help these sellers spend less time researching prospects. This workflow uses prospect emails to find their social profiles.

Coaching a lone wolf

How can managers help? They can supply resources and encourage the Challenger process. But let the seller choose how to execute.

Get to know your sales teams better! Automating customer persona reports helps sales reps quickly identify a client’s engagement patterns and other common themes.

Coaching a problem solver

These personas already gravitate towards the Challenger framework with their love for data analysis and problem-solving. Inspire them to keep going by removing process bottlenecks.

Do you have problem solvers on your team? Inspire them with a workflow that speeds up the research part. Use automation to qualify and enrich leads fast.


The Challenger sales model is about efficiency. Leave your feelings at home and charge forward based on the facts. It’s about proactively putting a halt to customer pushback and crafting a fresh storyline backed by in-depth research. 

The goal? Close sales faster by artfully guiding prospects away from the friction, and leaning more into how your offer impacts their bottom line.

By connecting workflows with automation tools, the entire Challenger framework is fine-tuned for agility and success in 2024. 

Try automating some of these workflows with Bardeen. All you have to do is download the Chrome extension and you can get started right away. It’s free forever and includes a 14-day trial of premium features.

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