Sally Ladrach
Table of Contents

As the Revenue Enablement Manager at thoughtbot, a global design and development consultancy, Sally Ladrach works to improve the sales enablement process and outcomes.

She believes you can only move the business forward strategically if you know the strategy or are deeply connected to it. In this interview, Sally discusses how she built successful enablement programs through cross-functional bridges, seller feedback, and empathy. 

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

Alignment, leadership, and priorities

We're all trying to figure out how to elevate enablement. From a day-to-day perspective, I'm always looking for and asking myself, “Are the things I am executing (or being asked to execute) in line with the priorities of the business?

That is where everything starts. You can move the company forward strategically only if you know the strategy or are deeply connected to it.

The answer to what the organization cares about usually resides at the executive level. 

Unfortunately for enablers, many of us are sitting in the role of sales enablement manager, sales enablement associate, or a more junior position, often without the right level of access to leadership. 

In smaller companies, you may have a direct line to the CRO or someone else in the C-suite. However, in larger companies, you don't have that direct line. The most important thing at this juncture is for enablers to build cross-functional bridges with the leadership and ask, ‘What are the priorities?

Suppose you are rolling out a new product and must sell ‘X’ amount. Hopefully, the organization is sharing the vision for the year, whether through OKRs (Objectives and Key Results) or goals. Being able to ask the C-suite, the reps, and your cross-functional partners what's important to them is crucial, alongside knowing organizational priorities. Ultimately, whatever you do inside your function, you must serve the people you work with. You will fall short of delivering on your OKRs and goals if you don't know what's important to the C-Suite.

Playing bridge

In my current company, I report directly to our CEO. One of my counterparts focuses on marketing and is a fractional CMO for some of our clients. While we don’t have a marketing function, when we need to tell people about our product, she helps them structure that marketing program.

The other major cross-functional partners I work with are the Managing Directors (MD), who are, by and large, our salespeople. They are responsible for bringing in business and for running their division of ‘thoughtbot.’ 

We are building bridges!

Enablement is the cross-functional bridge between business needs and rep needs. For instance, we have a division that focuses on creating new products and another on improving existing software products. Each of those MDs is not comped by commission like a typical sales rep. These MDs are responsible for P&L. They're balancing the budget of what they bring in, the utilization of their consulting team, etc. Essentially, I'm reporting to several CEOs.

We work similarly to how many software product teams are set up in that we have bi-weekly planning meetings where we say, “These are the priorities. These are the things that we're going to do in this sprint.” This could range from a small component of moving a bigger project forward or completing a larger project in those two weeks. 

The planning meeting focuses on getting things done. We also have another meeting called retro to discuss what we need to work on. What needs to be improved? What problems are people running into? 

We have a foundational value of trust and honesty. When people come to the retro meeting, they're ready to share what those things are, and we're prepared to discuss it and come up with action items together. It's been an effective way of assessing those things because, in my prior roles, I usually had to do these individually. This included establishing those relationships and building trust with sales leaders and directors. This has been a very different way to work, but I've been enjoying it. 

Creating successful enablement programs

When I started at any new organization, my first step was to audit the current state, which I did both qualitatively and quantitatively. I began by understanding the current state of the organization in-depth.


The qualitative way is to talk to everyone. When I started at thoughtbot, the first thing I did was talk to all the managing directors. 

What are we doing today? What are people struggling with today? I would find out if there was a specific pain point where they needed to hire somebody to dig in and understand that aspect backward and upside down. I spoke to everyone who interacted with it. I asked them the following questions:

  1. If I could do one thing for you to make your job easier or help you move towards your goals, what would it be?
  2. What roadblock would I take away? 
  3. What would I improve? 


From the quantitative perspective, I would audit the sales data. Whatever the CRM platform, I would learn how it works inside out because I needed to figure out the following:

  1. What data do we have? 
  2. Is it accurate? 
  3. What are the standard metrics that we refer to? (number of opportunities, close rate, etc.)
  4. What is the current state of these metrics? 
  5. Are we even measuring them? 

Figuring out what data you have so that you can build the systems to track them is the priority. When I entered this role, I fully audited all the marketing channels, including the website, SEO, Social media, and email marketing.

I did a health check based on five years of practitioner experience in different marketing roles. On the enablement side, I looked at the data. I did the qualitative feedback and decided to validate what I heard with the quantitative feedback.

Much of our data needed to be appropriately structured for me to validate. My first job was to rebuild the field structure and identify what we needed to do in our CRM to ensure we had the data required.


I told my boss, “I can't tell you what we should prioritize working on because we don't have the data to say that. So, getting our data in order is priority number one. Once I analyze that, I can tell you where our gap is and where we have the most opportunity for growth.

Building on seller feedback

Some of the most successful program initiatives I've run started with seller feedback. For example, I was in charge of the onboarding program in one of my roles. I made it a point to meet regularly with every new hire as they came on board, checked in, and asked, “What do you wish was better with this experience so far? Did this tool suit your needs? Are these learning modules too long? Is this too much at once? Was this session helpful, or was it a waste of time?” 

Checking in with reps and offering support goes a long way. The more reps trust you, the better and more authentic their feedback will be. While these are things they won't tell their manager or the CRO, sales enablement is the cool aunt or uncle. This feedback will undoubtedly influence how we design this program or content to ensure it's meeting seller needs. Otherwise it will be a waste of everybody's time if whatever enablement creates is not adopted.

What if you have hundreds of sellers inside your organization? What if you don't have the time to meet with people one-on-one? You need to get creative. 

Forming a sales enablement council is a great way to get feedback. For instance, at LocaliQ | USA Today, I ran programs for about 750 sellers and managers. The one thing I did in the most extensive program we ran was being consistent with surveys.  This wasn’t limited to sending out a survey after the program was finished. We surveyed after each program session. These surveys were short, taking about 30 seconds to complete. While people were still on call for that session, we said, “Here's the link. Go fill it out immediately before you do anything else because if we send it to you 10 minutes from now, it will sit in your inbox and go to the graveyard.”

This process allowed us to iterate on each session and make it better. Additionally, we could tailor those sessions exceptionally well by asking people what they wanted to learn about. I still get sales reps that message me on Linkedin, and they'll say, “I remember you. You did the ‘ABC’ training.” 

That was one of the best sales training we ever did and one of the highest compliments I could get as an enabler— creating something that provided value for the audience.

Enablement beyond onboarding

Onboarding should reflect the best practice for your entire sales process. That is the foundational standard by which all your sellers should sell. That shouldn't change between onboarding and ever-boarding. There is ‘how reps are taught to do things’ and ‘how reps actually do things.’

The challenge arises if how sellers are actually doing things is more effective than your onboarding program. In this case, you need to take this time when you're not busy onboarding people to fix your onboarding program and figure out what's working. 

Talk to your top sales reps. Dig into Salesforce and see which industries and business units are winning. Find the things that are working. Fix your onboarding program so that you're teaching. Take the time to teach reps the steps they'll use six months from now.

Let’s assume you have that gold standard. Now, if somebody comes to you with a new initiative or says the pitch deck needs to be updated, you have a set of critical assets that reps need to know. Those are the elements that you keep updated.

You won't know their real roadblocks if you do not talk to your reps or trust them enough to receive their feedback. Many companies make a huge mistake when they put a seller through three or four weeks of boot camp and certification and then tell them to sell. 

There's a huge wasted opportunity there. Sellers, especially if you're hiring someone experienced or tenured, will be disenfranchised by the first four weeks. They will try to check the box and say, “I just need to get through this. Put this waste of my time out of the way so I can sell.” That's not how you want sellers to look at your onboarding program. 

One of the best things we did was we had sellers doing their job from day one. We said, “Here's your list of accounts. Who do you know? What emails can you start sending out?” When we gave sellers a list of accounts on day one, it was like Christmas for them.

Reps have often never been in a company with a list of prospects to look at. If you hire experienced enterprise sellers who know what they're doing, they don't need the Sales 101. If you're working with more inexperienced people, you might have to have some of that in place before you shove them into training.

But they have got to start going through their account list, identifying the top accounts, and working with their SDR on the plan together. This will help deliver enablement for each part of the sales process. 

Week one

During the first week, reps are getting used to a new environment, catching up on pending administrative work, and finishing their training. This usually includes the following:

  • Understanding the culture
  • Finishing pending HR work
  • Completing training
  • Getting an account list

Reps can start looking through the account list and begin prospecting. 

Week two

Enablement will help reps get certified on the aspects they need to discuss. This means reps will know what they are talking about when those meetings get booked. I tell my reps, “If you book a meeting in week one and have a call next Tuesday and don't know what the company does or how to talk about it, it's okay. We'll get a manager on with you. Somebody will ride along. We're not going to leave you out to dry.” 

The sellers were so happy they could start doing their job from day one. Additionally, because they were being enabled on different topics while applying it, their retention of how to do those things was much better. 

Don't show reps how to put a quote together until they have to put a quote together. Don't talk to them about how to do a demo until they have to do it.

Reps: from good to great

Consider how much information is being thrown at reps all the time. For instance, the legal department says, “We updated this process. So next time you talk to someone, use this new language to use the right NDA.” On the other end, product marketing says, “We'll be launching this new product in a month, but we need you to start talking to your customers about it.” 

There are different ways to mitigate that. For instance, take all communication directed towards sales reps and put it in a single newsletter. That's one way to help hone their attention or help them know what to focus on. But, with the amount of information they get bombarded with, I would not know where to focus if I were a rep.

Apart from all this, their manager asks, “What's your pipeline? 

This scenario is just for one deal. Now multiply everything by the number of deals in the rep’s pipeline. That's what reps care about. Unless you say ‘ABC’ will help grow their pipeline, everything else will be secondary. 

Especially for transactional sellers, this is a lot of information. In an SMB, reps might have 10-12 deals running simultaneously. For someone not in a sales role, that might not sound like a lot, but if I think about trying to run 12 projects at once, that makes my head spin. 

Not just enablement but across the organization, we need to have more empathy for sales reps.

Situational enablement, creating space, and copiloting

While learning things in the moment has its place, it is also important to reference things in the moment. For instance, we put different things within this Sales Ops Slack channel. If there are common queries, we would find ways to surface those things when people need it, and that's also how you scale. 

Smarter Selling: Building a case for just-in-time enablement
Situational enablement for the win!

Leveraging those just-in-time, small chunks is a learning mechanism that works no matter where you are. 

We have this weird expectation with sellers that we can just thrust a two-hour webinar at them, and they're suddenly going to be better at their job. I don't want to watch a two-hour webinar, neither do you. Nobody cares about those two-hour videos on YouTube. Why are we expecting sellers to consume such content? 

For our reps, we had live sessions to walk through each piece as it happened. For example, we started with Salesforce 101. What does our process look like? How is that reflected inside of Salesforce? 

From an asynchronous perspective, we had support in learning from inside our LMS to supplement what the reps learned. 

We also had onboarding buddies. Everybody was assigned a buddy at the start because reps love learning from others. That is something I held close to my heart throughout my enablement career. Anytime you can have a rep educate a new rep instead of enablement, it will be much more effective. 

For that reason, we incorporated different examples or calls from our call intelligence tool to give examples. “Here's our top rep giving that first meeting pitch. You don't have to stick to the script, but here are the talking points.” 

There was a combination of live sessions, asynchronous learning, and supporting resources served at the right time while reps were doing a job. Additionally, periodic check-ins with the support team, whether it was me or an onboarding buddy for the manager. We had a check-in meeting for reps with their manager after 30 days. This was to figure out how they were doing across our leading indicators. 

Another vital thing our reps loved was having clarity over the following from day one:

  1. What were their goals?
  2. What could they do in the first 30 days to set them up for success when their ramp was over?
  3. How many meetings do they need to book? 
  4. What's their progress towards that? 

Reps need to know the right things to do to be successful. If you tell them what those are, they will go 112 percent to hit those goals. If they don't know what they are, it becomes that much harder for them to be successful.

About the author


Sally Ladrach

Sally Ladrach is the Revenue Enablement Manager at thoughtbot

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