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HubSpot Challenger Sale Agency Sales Skills Bootcamp Takeaways

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Takeaways from HubSpot Agency Sales Skills Bootcamp

Key takeaways we learned from from David Weinhaus in the HubSpot Agency Sales Skills Bootcamp, which was critical in helping us refine our sales strategy and sales process needed to achieve our agency growth goals.


310 Creative has been a whirlwind since we started in 2003, in all the best ways! We started-out as a marketing and web dev shop mainly for record labels, landing our first national account for back in 2005 for Virgin Records / EMI. As we focused more on digital marketing since 2010, our client experience has involved many household name consumer brands. As inbound marketing evolved, we started to focus on B2B and SaaS companies.  After becoming a Certified HubSpot Agency Partner, we have transformed to a more scalable retainer model.

Since partnering with HubSpot, not only has our client list continued to grow, but with some amazing clients that are exciting for us to work with. We have added a two new members to our team and continued to grow and reached Silver Tier within our first 6-months.

hubspot agencies los angeles

One of the things that’s really allowed for our growth to continue, is that we NEVER stop learning. Seriously, we are ALWAYS reading or doing things that will make us better at serving our clients. One of the major learnings we’ve had recently was in participating in the HubSpot Sales Skills Bootcamp.

I’m going to break down what we learned from our recent hands-on and intensive HubSpot Sales Skills Bootcamp. It wasn’t just us alone, but with a few other great companies, we learned an incredible amount about how to maximize our efforts for our client's results. With the help of our "professor" David Weinhaus  (@davidweinhaus) we learned a ton, and in this post, I want to share some of those takeaways with you—consider this me giving you the fast track to what I learned over the past 8-weeks.  Breaking down, to the best of my ability, our 8-weeks into something you can read over your morning coffee, your welcome!


The 3 Sale Sale

One of the big takeaways was the lesson the first week—we learned the 3 Sale Sale. It’s a tested process of learning how to really tell ‘your sales story’ and the three sales you really have to make to close a deal.  We’ll break it down into its three buckets and give some tips on how to succeed at each.

3 sale strategy

Sale #1: Why?

Change is hard for people, and every business has to evolve—but most people only change when they feel they really HAVE to make a change. So the first step is selling against is the status quo, convincing the prospect that now is the right time to make that change.

This starts with creating a simple Positioning Statement this sets the stage by telling your prospect exactly which problems you solve and for whom you solve them. You should make your own positioning statement with this simple framework:

We work with  ______ (type of company/role)

who____________ (aspiration)

yet are often________ (emotional word)

because of_________ (pain and/or problem)

Sale #2: What?

Now you have to help the prospect understand that while there may be many potential solutions to their problem—you are selling against all other solutions. What solutions do you use to solve their problems?

A tip here, you need to focus on outcomes, not tactics.  Don’t get too caught up in exactly what it is you’ll be doing—remember this is just the beginning of the sale! This is a good time to tap into emotion, be careful though because you need to use both logic AND emotion to tell a cohesive narrative.

Sale #3: How?

The final piece of the puzzle is to explain how you’ll be able to make this happen. Really honing in on what makes your company different. With whom will they be working? This is something that is often overlooked by salespersons, they forget that this is a long-term relationship, you want the buyer to feel comfortable.

Let’s recap that journey: you’ve helped them understand that now is the time to make a change, you’ve helped them to grasp what solutions exist, and then finally you take the time to explain why your solution is the best and they need to choose your company.

Find the Gap

A major focus for the second week was to understand what it means when you’re told to ‘find the gap’ this is the art of understanding needs. You could make an argument that understanding needs is the most important part of your sales process. The process of ‘finding the gap’ is really just a way of helping you organize your questions and assess true need.

Find the Gap Sales Strategy

This is one of the most important pieces that was hammered home during the boot camp. Asking questions is truly the essential piece of building trust with any new customer. Assumptions are dangerous in the sales process, they are often wrong and don’t make you seem smarter—but quite the opposite. Often you don’t really get the truth on the first question, so by peeling off a few layers, you get closer with every question to understanding why they’re even on the phone with you to consider your product or service. The more questions the more truth about that buyer’s real motivations.

There was an exercise we did in the role play of an art distributor coming into ‘pitch’ a hotel. If you look at the image below, we use the tactic of the “5 Whys” to uncover the real reason that the meeting even took place—but as you can see this isn’t answered immediately and took some digging.

5 whys sales strategy

You know that you’ve asked the proper amount of questions when you really get to personal consequences. One good tactic is to ask one or even two more WHY questions than you normally would. Not only do you learn about your prospect’s needs/motivations, but you show the client that you actually care and they notice this inquisitive nature isn’t just for show.


Selling Value on the Exploratory Call

The next step is to understand that this is really all something you can practice, and improve on with each call or meeting you take. It is important to remember that you will get more comfortable even if this might not feel natural to you when you start.

One piece that we talk about is the “Three Cs” these are the three legs of the stool: Client, Competition, and (your) Company. By remembering that these three are the pillars of the conversation you can maintain focus in your pitch.

The 3 Cs of Selling

There are 3 Tips we have for you on how to work well with some of the more taboo pieces of a sales call. These tips help you stay in the controlling frame of the conversation and don’t need to be tough answers when you set the frame and keep control.

Tip 1: Don’t Dance Around the Question

Usually, some questions feel a little early or hard to answer—but that’s why you need to address these head-on. For example, if you’re asked about pricing a solid response is something like “Jim, that’s a great question. For our clients who are looking for help growing leads and customers we typically charge between $4K and $10K a month” Give a short pause for them to hear this and take the opportunity to transition to a broader conversation “However, I wouldn’t feel comfortable yet recommending a specific budget. We usually talk a little more about what you are trying to achieve, your timing, and what resources you have to contribute. Then we can give you a firmer recommendation. Is that okay?” Then once this has been communicated, take a second to ‘check in’ and with a question like “By the way, is that range significantly different than what you were expecting I’d say?”

Tie-Down Questions

Tip 2: Solidify the Gap, Start with Goals

When you’re working with someone who has a goal, you need to understand ‘the gap’ and that means you have to start with the current situation—where they are today is really important to fully understand. You then establish their goals and take the time to understand timing as part of this greater goal. If you can fully understand their goals then you can work to understand what the barriers and challenges are in place. By asking questions you really can get to the heart and specifics of the situation at hand in order to put a strategy together to ‘close the gap’.

Exploratory Call Fundamentals

This week was all about how do you really make the most of your exploratory call with a potential customer. These often feel like make or break situations for many people, you’ve moved through the funnel to the ‘pitch’ on the phone. If you can follow some general guidelines this should be a smooth process and help to keep you feeling in control.

HubSpot Sales Strategy

Opening the Call should be a simple component, don’t get too carried away with small talk but do set the stage as a friendly call that will be conversational not just a sales pitch.

Exciting the Prospect & Gain Authority this is a really the main meat of the call, you need to remember that this is not the call to say EVERYTHING you know and have done. Keep it short and simple, this means to address any questions that might take you off topic but don’t ramble. This is a conversation—if you go two minutes without taking a breath you’re talking too much. A good practice to make sure you don’t talk too much is asking a check-in question like “Does that make sense?”

Closing the Call just keep it simple, make sure that everyone is on the same page. Good ways to do that are with questions like “What else were you hoping to cover?”. This makes sure that you didn’t miss anything and at the same time, your questions keep getting back to The Gap and understanding more about your prospect.

Using Homework Effectively this is the final step, which means that you take all the learnings from this call and put them down to fully understand how you need to move forward with this prospect.

Sales Call Recipe

Use these tips to create a good ‘recipe for setting the agenda’ if done properly you’ll enter the call with confidence, maintain that during a productive conversation, and have some takeaways that allow you to close the sale!


As we got into the second half of boot camp there was a renewed focus on role play and working through these learnings. Which I’ve got to admit, was a bit intimidating knowing this was coming…I usually don’t have other people watching me in my element. However, this was a great practice because it forced us to apply these new learnings—and one we ran through it a few times I already felt myself using the techniques in a smoother way without having to look at my notes. It became second nature and part of my organic selling process.

Sales Funnel Hubspot

4-Simple Steps

  • Step 1 is to ‘begin the call’ start with open-ended questions that help set the stage. This helps you to set a rapport early of trust and allowing your prospect to talk uninterrupted—organically leading to the next step.
  • Step 2 is all about understanding the ‘level 3’ what is the meaning of what your prospect is saying. This comes from asking even more questions—you have to dig hard to get the meaning behind the initial goals. If you haven’t set a rapport you may find your prospect retreat when asked harder questions, if they feel comfortable they’ll be very honest with you.
  • Step 3 is where you ‘find the gap’ as we’ve talked about its identifying what it will take to get from the current situation to the final goals, within a specified time frame. By doing this you’re beginning to talk about the plans that you would set in place and some of the challenges you know will come up—even before your prospect may know that will be a challenge.
  • Step 4 is about ‘selling value’ and a piece I haven’t talked about yet—anchoring. This is what really solidifies the power position in the call, by showing what the current situations are and options to move forward.  If you don’t set the anchor of the conversation yourself—then your prospect will and when this happens you lose a lot of your power in the conversation.

Exploratory Call Sales Strategy



As we wrapped up the final stretch of boot camp I was already seeing it’s positive effects! I was pitching more confidently, and really as I went through the practice on sales calls (non-role play) these truths of the pitch were becoming all the more self-evident. There is a real psychological reasoning for this formula of selling.

At this point, I just want to plug our teacher David Weinhaus and let you know that the HubSpot offers all sorts of sales tools & training!

The focus here is now on Goal Setting & Planning How to Advance the Sale some people refer to this process as a working session or preliminary planning call—if you’re already charging for your service at this stage then you’ll likely call it Road Mapping or a Strategy Session.

Challenger Sale Hubspot Pitch

This is a process led by you. It includes an assessment of current efforts, identification of your targets, and then a plan to hit those targets and the tactics you will use. Below are 2 tips on how to make this go smoothly:

Tip #1: Use a ‘Through Line’

You need to connect all of this into a single narrative, using a through line (usually revolving around visits/leads/customers) is how you pull it all together. When you do this you’re telling a story to the customer, not just a bunch of separate game plans or action items. It helps bring all of it together and back to why you are an expert that they should work with, you understand the full process.

Tip #2: Manage Expectations

This is about being smart about what you say, the last thing you want to do is over promise and under deliver—this will come to bite you later. Talk through the process and use your target numbers wisely. Targets at the front-end are not the same as outcomes after the process, but that’s why it’s important to use multiple outcome scenarios.

inbound marketing sales strategy hubspot

The final step of boot camp was to learn how to really close the business. This final piece can be broken down into three components.

Asking for the business if you’ve run a good sales process throughout then this should be fairly easy to close! However, you still have to ASK for the business and the best practice for this is to use a strategy called and Inoffensive Close. This is step #3 of the 3 Sale Sale.

3 Sale Sale Strategy

Objection Handling you’re not always going to close smoothly without a few more questions or some pushback—but again the more you do up front the better you can plan your work to avoid this problem. The reasons to handle this well are because you want to settle and diffuse any emotions which give you the best chance to succeed in the long-run.

LEAR method sales objections

If you hear an objection, you should be using the LAER method. This process helps by reducing defensiveness, lessens the tensions on the call, and ultimately provides you with an opportunity to be successful.


Offering the Right Solution (at the right time) now that you’ve made it past any objection and made sure that you specified what you’re offering clearly. It’s time to offer the right solution for this customer. It’s very important that you reflect on all the previous conversations and tactics used—don’t forget all of what has gotten you to this point. Building trust was important early and is more important now for a successful duration of the project. At the end of the day, you want to have a happy customer who loves your service and wants to keep you on retainer/use your service for a long time! Working together will not end after the sale, it’s just the beginning, make sure you make your customer happy now and it’ll pay dividends down the road.

Key Takeaways

If sales aren’t natural to you don’t worry—you aren’t born with it, it comes with practice and knowing the right tactics. Just like any other activity you need to know the basics to excel at it. If this is something you want to learn more about seriously consider taking the HubSpot Sales Boot Camp—I like to say that it was like taking Drivers Ed, it gave us the education and tools we need to eventually drive Indy cars.

There is a ton to learn in sales and if you put in the time you’ll be able to succeed—at the end of the day anyone can learn how to excel here! We’re now certified sales LIONS and excited to put our new learnings to the test as we bring on new clients—if you want to hear more about our experience or are interested in what we’re selling click the link below and chat with us!


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Chris Leach

Digital marketing professional with 17-years of tested experience balanced in strategic planning and scaling ROI for lead generation, customer acquisition and client engagement programs. Since starting 310 Creative in 2003, I have had grown it into a Platinum Tier HubSpot® Partner ranked in the top 3% of all HubSpot® partners worldwide and serving as an extension of marketing teams of large brands such as Live Nation and Universal Music Group to help scale marketing and lead generation partnership campaigns for Verizon, Best Buy, AT&T and EMI.

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