Samir Doshi
Table of Contents

Samir Doshi, the Director of Sales Enablement and Sales Training at simPRO Software, started in sales before transitioning to sales training and enablement. His favorite pet project is helping sellers sharpen their game and unlock easier access to helpful experts through HelpfulPeople

In this interview, Sam talks about prioritizing reps and the metrics and behaviors that matter. Sam believes keeping it simple, leveraging a data-driven approach, and being yourself are essential to elevate enablement today.

(This conversation has been edited for length and clarity.)

Elevating Enablement

Elevating enablement comes down to job security and feeling good about what you do for the community. What does it mean to make an impact at the end of the day? When dealing with the Executive Leadership Team or the sales leadership at the C-level, it comes down to two things: the investment and the ROI. 

However, the company needs to foster a good work culture. Bottom-line improvement at the sacrifice of culture is not sustainable. We have all had jobs where we sit next to somebody, cold call prospects, and we don't see them the following week. That places a tremendous burden on training and onboarding. 

One way to do this is through an executive slide that can be sent to any executive or tailored for them with the following information:

  1. What did sales enablement do to maximize and close the sales execution gap or any execution gap? 
  2. What does that look like? 

This could mean productivity or revenue. Suppose you have had new reps join this quarter, and they closed deals in 5 weeks versus 8 weeks at a pace similar to the pre-enablement era. Maybe they used to close USD 80,000 but now are closing USD 120,000. 

The first service you provided to the C-Suite executive was that they did not have to do that math. Enablement can do this math for the C-Suite, with all the data at your disposal, and validate it. Reaching out to get BI folks to help you do the math will go a long way in social capital and showing impact on dollars. 

As long as you're caring for the holes in the boat and the boat is going faster, we can get more comfortable seats. 

Enablement, the C-Suite, and prioritizing reps

Enablement needs to infuse clarity over the metrics into the system as a service. The company is essentially paying you to get educated. Enablement needs to have just 25 percent faith in what they are doing and tell the right stories for people to believe in coalition within the company. For instance, if there is a cohort of reps, it is important to consistently have coaching touchpoints, whether the front-line manager or a sales coach. Reps who get less than 30 minutes of coaching per week close deals at a rate of 43 percent.

If these sessions can be increased to two hours per week, their closing rate is 53-56 percent. That’s a nearly 25 percent increase when applied to their pipeline and is a great outcome that can lead to an expansion of enablement. Once you start proving that, you can go to leadership, “Let's get some budget for 2024. We are seeing that we can improve this, so you can see how we can stitch the story together in a very compelling, meaningful way.”

You need to fill the jar with the right material. There's a learning quota with effective learning series and gap-based training programs tailored to the individual. With the right LMS and apparatus, sales effectiveness can be increased by using technology to create a personalized experience. 

The reps are enablement’s primary customers. When considering econometrics or productivity, prioritizing what the rep cares about needs to be prioritized. Some reps are sometimes forgotten in this equation. 

Reps change the C-level. 

Let’s go with a sports analogy—the Warriors, for instance. Everybody's pretty interested in Steph Curry. They are also interested in Steve Kerr. But maybe keep Steph Curry over Steve Kerr at the end of the day? Before everybody gets mad, let me explain what I think and why. 

We need a star player more than anybody. You see more of that focus, and reps deserve that attention. They're at war, but people are looking for the live boats when things get chaotic out there. In a chaotic business world, people might not know it themselves, but they need sales reps. They need advisors to figure things out. It's not a compelling reason or purpose. Reps are assets. They want purpose, live for driving value, and like posing the deal, not just for the money.

Upskilling reps for today

Sometimes, you want sales cycles to be longer because you get more money and value. Sometimes, if it's a large enterprise deal, you need to teach the organization if the buyer knows what they are refusing. 

What's the sweet spot of reps knowing enough to be dangerous but not enough to drown in knowledge? 

Sales Readiness

We must be smart in showing the rep because they won’t have time to study other patterns. 

  1. What is the pattern intelligence of how best to pace and approach your business as a mini CEO? 
  2. What's going on in the world and your industry? 
  3. How can you run your business as a mini-business? 

The middle layer between readiness and effectiveness is awareness. If a rep takes their pipeline value and applies it to the marketplace, their pipeline is more valuable than most small businesses in the US or globally. 

If reps don't think of themselves as mini-CEOs, they do themselves a disservice. The overhead is taken care of by the company. With reps running a USD 4 million pipeline, sales readiness is the investment, the hours of coaching, and the learning required to close deals.

Sales Effectiveness

If you are giving inbound leads and trying to get to them in under 5-10 minutes, there's a high-velocity gain from the moment reps have that demo call to when they are closing things. Here are some questions to consider when the priority is speed to lead across the funnel:

  1. What are your funnel metrics? 
  2. How is your pacing? 
  3. Do you have 4x coverage? Does your conversion rate support that? 
  4. Are you converting, and at what speed, amount, and volume? 

Apart from the above, are you keeping pace with what is happening in your and your client’s domains?

  1. Are you aware of what's going on? 
  2. Are you making investments and feeding reps industry information through your business acumen?

Value Addition

The client is often forgotten after the deal is closed, leading to the sales funnel being neglected. However, the client signing on is special, which needs to be kept in mind. 

What can you do for this client? Can you send them something? Can you just call them? For instance, I set out a challenge as a sales manager at Persado. I told my reps, “I want you to have quality conversations because I believe you are high-quality people. Why don't clients just call you out of the blue because they want to talk to a smart person who will help them?” 

We just put that out there and started getting clients calling us out of the blue, “I had a quick question,” because reps began to tell clients if they have a question, they want to be valuable. Beyond the core set of required health metrics, some proxy things buttress them. 

  1. Are clients calling you? 
  2. Do you have a book of business? 
  3. Do you have 10 clients you regularly keep in touch with? 
  4. Are they your advocates? 

What are you doing for the community? Are you out there providing value? It doesn't mean you will get anything, but this is where the soulful piece will stand out. AI and other things will take care of the mechanical stuff. But the spiritual side isn’t something that AI can inspire. 

You can buy a fake Rolex and have it look exactly like the real deal. But you know it's not the real thing. That makes a big difference. Human interaction will continue to be the main focus. People have an appetite to do good for each other in the community, and we must focus on that, too.

Data, reps, and enablement

Everything has to be audience-driven. A seasoned rep of 10-20 years doesn't pitch. The most important thing in sales is that it's not about you, your product, or the talking. It's about the buyer. This changes the game because you do care. The same thing can be said for internal stakeholders, and it has to start with the top line of what enablement is doing for you. 

The first thing is data. If you are talking to the CRO, here's a breakdown of your organization:

  1. What did you expect?
  2. What are we producing today? 
  3. How are we training over time?
  4. How much revenue is coming in, and how fast?
  5. What is the rate of churn? 
  6. Who’s hitting quota? Which reps aren’t? Why?
  7. How much of the team is performing?

After you have acquired a customer, you need to take care of them. If they are the right fit, ICP-wise, the last thing you want to do is lose them. Why are they not staying with you? Can you leverage that information into other conversations to be proactive about these leaks? 

What is enablement doing from a group force standpoint? 

Keeping it simple

Often, companies like to brand their own language and be coded because that is how you become thought leaders.  However, today, people no longer trust coded language. You will instinctively know when you're losing the audience as a rep or sales leader. How can you tell them in simple language that you are always looking to improve? 

Keep it super plain because you have to understand the audience. This isn’t the only slide the CRO will be looking at today. You are lucky you get five minutes with them. Going forward, you might earn ten minutes. Earn it, and you might get 30 minutes. Then, before you know it, they will call you, saying you are valuable. Here is my advice for BDRs. 

  1. Playbook is just a calibration, but personality is also crucial. The more you're yourself, the more you can convert. That's how you stick out. Be yourself, and that's the easiest thing to sustain. 
  2. Eliminate the effort for the audience—zero strain. For instance, when you look at an email, you size it. In a nanosecond, you know if a specific email will be difficult or delightful. Based on the presentation and the optics, the initial first impression is the last. 

If you can project a vibe of zero effort because you have intentionally removed the pain points, this is high value, high gain. It's economical for them to work with you. With lower effort every day, higher output, and higher gains, people will gravitate to this. That's the ideal vibe for sales teams. You work with this person, go faster, and sweat less. Who doesn't like that?

The essential behavior and metrics  

Behaviors are difficult to sustain and reinforce when we lose. Suppose you ask someone if they want to be more effective, and if they want more by doing less, the answer will be a resounding yes.

But, they wouldn’t want to go to training if they don't believe in it. Training has traditionally never been for the audience. It's typically been a checkbox item that a poor stakeholder needed to deliver. While everybody in the sales enablement community is trying to solve this problem, a culture of audience-centric, seller-centric, and bespoke micro-training is slowly growing.

A modern learning approach exists because people have come from being treated generically and don't want to perpetuate that. Behaviorally, let’s break it down into two triangles. 


First, you need clarity on what you are doing. Everybody needs to be aware of change management. 

  1. What's the methodology? 
  2. What's the competency? 
  3. How are we going to coach the rep who needs to understand that? 
  4. What's going to happen, and how?
  5. Why is X happening? 

Reps deserve to know the why. They need to be oriented. For instance, if you talk about pricing for 45 minutes in a 60-minute conversation, you have a 65 percent chance of getting your next meeting on the books in the next week. This ties back to lower effort, higher output, and validation. Now, Gong can be leveraged for a better understanding of your reps and how to improve.

You can provide that validation to your reps in the first slide. “This is why we are here. This is the best knowledge of the competency and the coaching we will put in place for you to capture this fruit, and this is what it means to the buyer.” 


While every training starts with the actual training, that's not where reps learn. That’s where they become aware. Their behavior changes slowly in the next 90 days, 6 months, and the next year. Enablement needs to know and accept that there won’t be a significant change in behavior. They won't be able to change 15 behavior patterns in 15 days. They can change maybe two or three significant behavior patterns in a year. What do we want those to be? 

Storytelling is essential. It starts with communication and the ability to listen actively—there are multiple soft skills. The next aspect to focus on is the ability to close a deal. This comes with objection handling, knowing the business, and being able to walk somebody through the important aspects of your product. 


Bring value and data validation to your relationship with the frontline manager. Build a relationship with authenticity. Here’s what standard selling looks like, “I want to understand your business. What are your personal and professional goals? How can I help or not help? Am I the right person, or not for this?” 

You need to discuss the negatives, as well, to do good work together. If you're in a new team, a discovery conversation with all your stakeholders at least once a quarter is non-negotiable. The business will be drastically different three months from today.

If the sales manager admits these are important and they want to work with enablement to improve these aspects in their team, you have your yeses—time to go and develop your training. 

You have to spend more time over the next 90 days on the reinforcement. For instance, when working with VDRs, I'm very transparent in my slide decks. My first slide will say, “Here's what went into the design thinking.” As I continue to show them the work, “This is why we chose to do this. Here is what is in it for you.” During the training, I will say, “ABC is the reason why we're going to do this training for 4 days as part of the onboarding. However, we will spend more time over the next 90 days, and you will have a chance to speak with me every week. I want to hear from you.

Being yourself

You have to bring your personality and be yourself. You don’t need to yell or be loud. The best enablers are the ones who are authentic. People are smart; they can see when you are putting in effort to check something off a list or because you are prioritizing them.

Reps need to know that you prioritize them. It starts with having a conversation with yourself and asking if you actually care about this job. Why are you in it? Are you in it for yourself or the reps? That's the start of it. Enablers are the difference-makers.

As an enabler in sales training, finding a passion for this is fundamental. If you are not passionate, you have to get out because there's an opportunity cost. If you are training reps, it isn’t a neutral setting. You cannot be a drag on the business and their lives. It needs to be serious. Enablers have a job where they need to grow and progress with other people.


It's often chaotic when enablement comes into a startup or new business season. We are shifting from a jazz band to an orchestra, which takes immense coordination. The alignment, communication, and advancement need to be on point every step of the way. 

Enablers need to be sweating about who doesn't know what they need to know and why they don't know it. This is difficult, but you can build this muscle, and it gets to a point where the paranoia can be good and productive. 

Does this sales manager know exactly what this training will be about? How can I explain within three bullet points in Slack so we don't have to have a meeting about it?” 

While learning how to package information in headlines and bullets took me years, I'm still learning. Overcommunication is excellent because it triggers your intentional effort. Reps can see you are working hard on their behalf. “We are in this together.” 

Clarity and alignment help with being able to devote yourself and contribute to the community. How you pack and ship information needs to be audience-centric, almost like a fulfillment warehouse.

About the author


Samir Doshi

Samir Doshi is the Director of Sales Enablement and Sales Training at simPRO Software.

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