Accidental enabler Rachel Ha’o, Global Sales Enablement at growth marketing platform, Iterable, talks about juggling glass balls and rubber balls, explains why virtual onboarding is like building with Lego in the dark, and shares her top morning tip for prioritization.

Q. Tell me a little bit more about your career journey and how you came to work in sales enablement.

A. I came into the world of sales enablement by moonlighting as an enablement person for quite some time before I moved into it officially. For several years, I’d been an SDR, I’d been an account executive, and I remained the top performer in those roles. At the same time, I had been working on materials to help train the team or documentation to bring everybody along, as well as my own FAQs for engagement that was then shared amongst all the account executives.

It was what I thought was needed for working in the size company that I was at. When we had some leadership transitions, I was approached by a new VP of Sales, and they asked me if I considered moving into enablement full time.

I sometimes think the assumption is that enablement is where account executives go to retire - and that is definitely not the case! I moved into enablement because where I found most joy was at the intersection of finding a challenge with the team and then being able to develop a solution for them and watch them adopt that solution. Live in the wild, so that they could own success and that was more exciting than closing my own deals.

Q. When you say you were moonlighting in the role before taking it on officially, did you know you were doing sales enablement?

A. I had no idea. I believe that sales enablement is still relatively new and nebulous, especially in other industries outside of software, or SaaS, and I thought I was just being a good teammate: “Oh, people have a question? I'll find the answer to that”.

But now, it turns out that it’s much more than that. There’s this whole world of instructional design and learning theory and analysis that goes far beyond just creating docs or guides.

Q. What would your own definition of ‘sales enablement’ - in a nutshell?

A. Let's see if I can keep this concise! So enablement, to me, means leveraging hard skills, and sometimes certifications, in instructional design and adult learning theory such that you're able to identify a knowledge or skill gap that individual representatives on your team are facing. Then developing a training program, a methodology, or framework that adequately addresses those challenges with a solution that they're able to acquire for themselves.

What that looks like in terms of a mission statement, or a charter or something more aesthetically pleasing? I would say is sales enablement empowers customer-facing human beings to be their best selves at work.

Q. In today’s virtual world, what ways have you found useful to onboard new employees, to get them engaged and ready to sell?

A. Great question. I'm going to back up a little bit, and it might seem abstract at first. The way that I have adapted onboarding and communication strategies for new hires is by first giving them a lay of the land. So they know why the communication strategies and channels I propose are important and what their onboarding programs are generally going to look like.

The analogy I use for that is onboarding, whether in person or remotely, is a lot like building a Lego. If I just gave you the pieces, and didn't show you the box, and didn't give you instructions, it would be pretty challenging to build the Lego the way that you're supposed to. You can build something, but it might not be what you wanted.

Onboarding is the equivalent of giving them a picture of what onboarding and the end result is supposed to look like. We give them the instructions, we ask that they follow them, at least for now. And then we can move on to the master builder later on, building on what we’ve taught them.

Onboarding remotely is actually more akin to someone building a Lego in the dark. So, I know you are building your Lego, but I have no idea what you're doing or how you're doing it.

I don't know if your workstation is set up for you to even build something effectively. I don't know if you have a situation like me where my cat sits on my desk, and so you don't have enough space to even build a Lego!

So, we've set up all of our new hires with a dedicated Slack channel. We give them the rules of engagement for the channel, for example, we have a class that started yesterday, and the expectation is that the enablement team posts at their beginning of the week and at the end of the week, with what's to come, what they should have accomplished and what they're going to look forward to for the next week.

Just doing those simple check-ins virtually promotes discussion and people start to break the ice and feel comfortable asking questions. We also meet with them regularly. We set up live training sessions, where the last half of the meeting is always dedicated to them asking questions.

We also use a learning management system (LMS) where every module has a section for them to enter questions that they might have had, after the learning is over.

So just providing those touchpoints and letting them know it's okay to have these questions is important because, again, I don't know if you're having trouble building your Lego after we hop off our calls.

Q. In that Slack channel, whose responsibility is it to interact and respond to the reps’ posts and questions?

A. You're touching on something very interesting, which is frontline manager responsibility. In onboarding we don’t have frontline managers included in the Slack channels. There are three to four enablement people in the Slack channel, in addition to sales operations, and potentially someone from HR.

Later on in their ramp period, week five or week four, when things become a little bit more technical, we may add subject matter experts like solutions consultants or engineers to help answer any technical questions that come up.

The frontline managers follow sales enablement’s ‘new hire manager guide’, which outlines everything that's needed from them from week one through week 10.

Q. Which departments does enablement interact with the most on a day-to-day basis?

A. It depends on what's going on. During onboarding, I would say I interact mostly with HR and the new hire frontline managers. The reason for that is that Iterable as a company onboards all employees in orientation cohorts, and it's extremely important that I'm aligned to those onboarding dates in their program.

Enablement isn’t the primary onboarding motion, so coordination with HR is extremely important, and the same with the managers to keep them up to date on new hire progress, discuss roadblocks or challenges, and even provide praise - a lot of our new hires do really well, it's important that their managers know that.

Outside of onboarding, if we're working on a sales process, sales methodology or something like a revenue kickoff, I personally interface most with subject matter experts from all different departments like product marketing, sales, operations, frontline managers, and then sales leadership - our VPs of Sales.

Q. We were talking earlier about how things have changed since the Covid crisis began. What does a typical day look like for you now? How is it different from before when you were in an office environment, working face to face with reps and your other colleagues?

A. For me personally, I have had to be more diligent and ruthless in the way that I prioritize my time. My manager is incredible. I'm not quite sure of the magic behind what she does.

There's a trick that she gave me: at the beginning of every morning, I draw a quadrant in my notebook, and I'll mark at the top left ‘do today’ then, in each square, ‘do end of week’, ‘end of quarter’, ‘end of year’. So, as things come up throughout my day, I can write down what type of priority it is.

Is it a glass ball where you know, I can't drop this? This has to be managed today, I absolutely have to keep juggling this. Or, is this a rubber ball? This is something that I can let fall and bounce and nothing will happen to it, I can come back to it at the end of the quarter.

Protecting my time in that way has been the biggest shift for me, because you need to expend so much more energy to get things done. Your cognitive load is super impaired by being virtual all the time for everything you do. And, very quickly, time becomes your most precious resource.

Q. Your journey into sales enablement was quite unusual, because you started doing it almost accidentally. If you had to give advice to someone who was just starting out, or thinking about moving into it as a career, what would that be, based on your own experiences?

A. Really great question. What I would tell anyone who's starting is: “Know why you're moving into sales enablement, and know the expectations for you in that role”. The reason I say that is, I was a top performer as an account executive. And I thought the reason why I was being asked to do enablement is because I made a bunch of resources and the leadership team wanted me to train other account executives to sell the way I was selling, because it was working out for me.

That is the fastest way to be unsuccessful. Absolutely do not train other people to be copies of you.

Everyone has their own superpower in sales. Sometimes it's a little harder to find out what that is. But that's the role of sales enablement, and frontline managers.

One of the things that is most exciting to me about my job is not asking people to try something that I tried, or to do what I did, but to discover what works for them, and their process, and amplify that and help them crystallize their own sales motion within the boundaries of what's expected.

Q. What career backgrounds do you think will prepare someone with the right skills and the right attitude for sales enablement?

A. You have to be very humble. Humility is a cornerstone of the attitude you need to have in enablement. And in terms of the right background, I'm biased because I was an account executive, and there are insights as to what motivates someone in sales as an account executive, trials and tribulations that you face that give you a sincere understanding of what a salesperson needs to be successful from training, or from a company, or from their manager. If you haven't done the job, I think it's really challenging.

That said, people move in from customer success, people move in from learning and development, and from HR to sales enablement, so I don't want to diminish anyone else's experiences or say that you can't move into it as a career if your background doesn't look that way.

But I would say that if your background doesn't come from a traditional account, executive or customer-facing revenue-generating role, spend a lot of time with those people to really deeply understand with no judgement, what it is they do and how they operate and what motivates them, what frustrates them, and what really gets under their skin - and then go from there.

Q. The past year has been a learning curve for us all. What has been the steepest learning curve in your career overall?

A. I was trained and certified in traditional sales enablement, which means you first determine what your learning objectives are for everything that you do. That needs to be the North Star of the content of your material or training, even the way you interact with sales leaders, really pushing and challenging them to ask “What is expected at the end of this?”, “What do you want the customer-facing human to be able to do?”. That will definitely add more rigor to the way that you create content. And the expectation then is that your content is of extremely high quality.

2020 was the perfect storm for a lot of reasons for a lot of teams. What I learned, and what is challenging for me, is that you cannot let perfect be the enemy of good. Oftentimes, something is better than nothing.

As long as you're not asking people to unlearn material and relearn something different later. If you push content at 75%, and then iterate on it later on, improve it later on, provide reinforcement exercises later on, that's okay, that's kind of what we need right now.

And learning to just ‘get out of my own way’ I would say is a challenge that I face pretty regularly. But I didn't anticipate that I would face it, until I was already in the midst of creating a deck and realized, “This is due and what's expected of me has changed!”. I need to just adapt and be flexible and move forward with what's good for right now.

Q. What's your content creation process? Who decides what content is needed? And who actually creates it? What's the process at Iterable?

A. The process at Iterable is twofold. There are two different ways to determine how we build and launch content. The first way is the company as a whole does a great job of setting company-wide objectives. So we determine what our strategy for the quarter for the year is going to be and, from there, the executive team, our C-suite and our VP levels, determine what their OKRs are going to be, what their performance objectives are going to look like.

Those are distilled and communicated down to my manager, me and the rest of my team, and all the middle levels across the board, for us to work on specific projects that can contribute to those objectives and key results.

The second way is, things come up throughout the year; for example, solutions consultants are on calls with account executives, and they both decide “Wow, wouldn’t it be really great if we could learn more about coding in JSON? A lot of us need help with this”. Then they will probably submit an enablement request form, which is a Google Sheet that reports to Asana and outlines the type of content that’s being requested: is it a training? Is it a guide? Is it simply a doc or a spreadsheet? What's the priority?

We really ask people to look back to those executive level goals and make the connection between what training or content they're asking for and how it may contribute to the executive initiatives.

Then we determine the audience, the mode of launch and, depending on what the learning objective is, the enablement team will decide who the subject matter expert for the training will be. If it's something that has to be done live-recorded, put into WorkRamp, or can simply be a Guru Card (which is like a Wikipedia article that people can read later on).

Q. Do you ever find it of a challenge to actually get salespeople to be honest and transparent about identifying their training needs?

A. I actually have the opposite challenge, where people are coming to me with a lot of asks, and I'm very fortunate that I work in a company where one of our values is humility. Another value is a growth mindset. So people are constantly in that mode of “How can I get better? What do I need to learn?” and raising their hand and identifying those things. So I have the opposite challenge.

Another challenge is that not everyone's training needs are the same. So we might have mid-market account executives that would really love to be trained more on prospecting. We might have enterprise account executives for whom prospecting is not really a high priority because they work with an SDR, and what they need help with is pricing and negotiation training. Their roles are very different, and their skills and expertise are different, so what they need is very different.

But there's only one of me, and it would be really challenging for me to build two different types of training within the same timeline. So I need to think about which one is ‘the heart attack’, which, which one is the bigger knowledge gap, and which one's ‘the broken foot’? Going back to my quadrant, I need to think, okay, I only have so many hours in a day, what should I get to first?

Q. You talked about there being a culture of wanting to learn and wanting to grow at Iterable. When you don’t have that face-to-face office environment, how do you maintain that culture?

A. How I maintain it for myself is I tried to be very diligent about asking for feedback from reps, from my manager, from my manager’s manager, from frontline managers that work with the sales team, then writing it down and going back to the team and asking how we can inspire that.

I don't have a fancy strategy. For anyone that's interested in inspiring a growth mindset and maintaining it remotely: know your team and know their culture, and find creative outlets where you can promote a type of feedback loop or highlight wins. Salespeople love competition, so making things a little bit competitive is a forcing function for people to seek out feedback or to seek out best practices and adopt them for themselves.

An example of this is we send out a Wednesday email every week that highlights the best prospecting strategies, meetings, books, deals, closes, the best calls, highlighting discovery wins, demo wins, teammate wins, where SEs and AEs have worked really well together. And it fosters that culture virtually because people want to be in the email, people want to speak up weekly in our team meetings.

This means they will naturally seek out what other people are doing that's making them successful, and ask “How can I adopt that for myself, and what do I need to do in order to be better and be featured in one of those wins?”.

Q. Final question: how do you see sales enablement, transforming over the next few years as a practice?

A. I've been thinking a lot about this lately, because our role changed a bit over this past year. Where I see a gray area - not just with what I do, but with what has bubbled up from other sales enablement communities - is that there is a fair amount of overlap in what we do and what sales operations does, in terms of bringing motions to life in practice.

I do see a world where there could be ‘Sales and Operations Managers’, or ‘Sales Enablement Operations Manager’, or VP levels that oversee both functions, like a ‘Vice President of Sales Enablement and Operations’.

There's a couple companies that do this really well, I think Segment is one of them - they have a Vice President of Sales Enablement and Operations and their teams move in lockstep. And that's the direction that I think the role itself will go in: more strategically, in the methodology world. I see a lot of evolution in the years to come.

You can listen to this interview with Rachel as part of our Sales Enablement Innovation podcast series - or catch up with all our previous podcasts here.