#1 on Inc. Magazine’s List of 50 Best Websites for Entrepreneurs
#2 on Forbes List of 100 Best Websites for Entrepreneurs

A Strong Team Starts at Onboarding




An Interview with Andrew Quinn of HubSpot

Having a high performing team means:

  • Hiring the right people
  • Creating a structure and culture for them to do great work
  • Equipping them with the knowledge and skills to work effectively

These first two topics have received a lot of attention in the startup community. In fact, I recently wrote a post on this former topic discussing why startups need to build their hiring muscle internally.

But, where I’ve seen less discussion is on the topic of employee onboarding. As a founder and first-time CEO, it may be tempting to skip over this topic (and not read this blog post), as you may find yourself assuming that all the hires you make will just figure out what to do on the job. This is a serious mistake, as it will take far longer for your new hires to become effective, and you are likely to miss your plan as a result.

Nowhere is this more important than sales. As I talked about in my previous blog post “The Irrefutable Math behind Sales and Marketing”, the bookings numbers in a B2B company are heavily dependent on being able to recruit salespeople on time, and ramping them to full productivity over a short period of time.

Investing your personal energies in getting a great onboarding course can have huge paybacks. Don’t be surprised to find that you are likely the best person to explain the customer’s pain point, and the company’s vision for how to address this. You are also likely to be the best person to describe the culture you want to build. So invest your own energy in creating these parts of the onboarding course. It’s the most scalable way to pass on the valuable knowledge that you have locked up in your head.

HubSpot as a best practice example

I wanted to use a real world example of a company that does a great job in this area as a way to tell this story. Fortunately one of my portfolio companies, HubSpot, has a really great onboarding process, which was largely due to the work of Andrew Quinn. Andrew was kind enough to allow me to interview him, and what you see below are my questions and his responses.

Why is sales onboarding so important for a company to get right?

A great many companies obsess over how to scale the sales model. Very few obsess over how to scale the sales behaviors that make the model actually run. Those behaviors involve the questions asked, the value statements that are made, and how objections are addressed, to name a few. Getting these behaviors consistently right is the key to scaling your growth in a predictable way.

It’s really just simple math. Let’s assume you hire your first three sales reps this month and they complete three sales calls a day.  That’s 45 calls in five days.  Extend that over the year and you’ll have 2,340 sales calls for that three person cohort. And, if you’re scaling your team and hiring three people every month, you’re looking at 15,210 sales calls over the year. That’s fifteen thousand sales calls where you are applying consistent, predictable sales behaviors that lead to your desired results, or fifteen thousand individual experiments, some which work and some which don’t.

Where should a company start when creating an onboarding process?

It starts with being very clear on what each person needs to know to have what I call “baseline viability” in their new role. I spend a lot of time up front figuring out what the core knowledge points and functional skills are that a new hire needs in order to hit their desk running and start making a contribution without needing to interrupt the work of others.

onboarding 1


Obviously onboarding is never going to give a new hire everything they need to step into their new role and deliver the same level of performance as someone who’s been doing the job for a while.

The goal should be to give new hires all the things they need to ramp quickly and successfully in their new role at the company.

Once you determine what will get someone to baseline viability, you can back into what has to be included in an onboarding program to deliver a consistent learning experience for every new hire.

For every company it will be different. In fact, onboarding will most likely be different for various functional groups within a company. Let’s say you hire salespeople, developers, customer success reps and tech support engineers on a regular basis. While they are all heading into different roles, they will need an introduction to the core information about the company they are joining. Once they have been exposed to that information, you have to ask yourself “are they baseline viable for their job yet?” Depending on the role, some of them will be, so their onboarding is done. For others, they’re not even close. That means their onboarding needs to continue. Therein lies the challenge of a successful onboarding program. How do you create baseline viability consistently when it’s different for each functional group?

How does onboarding work at HubSpot?

The easiest way to describe the process is with an illustration.

onboarding 2


We found it valuable very early on in the company to ensure everyone coming into the organization had the same foundation. All new HubSpotters go through the same three day initial onboarding process that introduces them to our culture and provides insights into how the business works, who our customers are, the products we produce, how we market those products, and how we sell them.

After the first three days, certain job roles peel off from training and head to their respective areas for more team-directed training based on their area of specialty. Those who need detailed working knowledge of Inbound Marketing and our software products remain in training for a deep dive into those two focus areas for another four days.

At this point, certain job roles again will peel off from training and head to their respective areas for team-directed training. Those who remain are all in customer-facing roles that require in-depth training to provide them with the core knowledge and skills to get them to baseline viability. Since these roles focus on different areas of the customer relationship, training now splits down several tracks.

How did you get to this point?

Tell us a bit about when you joined HubSpot, and what the situation was at that time for onboarding?

I joined HubSpot in July 2009. There was already a basic onboarding program in place with a lot of self-directed learning. Sellers at HubSpot need to master three areas of study to be able to sell effectively: 1) Inbound Marketing best practices, 2) the product and 3) the sales process. A significant portion of the inbound marketing and product training centered around watching videos, reading blog posts and meeting with subject-matter experts. Sales training involved text-heavy PowerPoint driven lectures focused on different aspects of the sale along with sales call observations.

While we still focus on these three areas of content, this early onboarding program had a number of fundamental flaws that were beginning to create inconsistencies that were adversely affecting our ability to scale.

If you’re evaluating a current program, I highly recommend going through the process as a learner yourself.

By going through the program as a learner, I could see that while the content was solid, there were issues with the learning methods applied to particular knowledge or skill areas:

  • The sequence of modules made it difficult to get a clear picture of how all the different subject areas tied together in the context of the sales role.
  • There weren’t ample opportunities to practice and apply what was learned.
  • The space allocated to the training environment was wholly inadequate.
  • The tools to measure the program were misaligned.

How did you go about creating a consistent onboarding program?

The first thing I did was to identify what baseline viability was for our salespeople. I spent a lot of time with sales leadership figuring out what a new hire needed to know in order to get on the phone, have meaningful conversations with prospects, and be effective on the job. I then imposed these knowledge requirements against a “reasonableness test”–stack ranking all of the knowledge and skill areas by how critical they were to the sales process and then asking “how reasonable is it to expect someone to learn this particular knowledge or skill within the time allotted for training?”

We started with a six step sales process that we believed salespeople needed the necessary knowledge and skills to execute on:  Research, Prospect, Connect, Discover, Demo, and Close.

onboarding 3

We then stack ranked these skills and asked the reasonableness question. We quickly discovered that while Demoing and Closing ranked very high, it was unreasonable to expect someone to learn these skills within the new hire sales training window given the complexity of our sale. Keep in mind, new salespeople also had to develop expertise in Inbound Marketing and our product during their training month. In addition, it was highly unlikely that a new salesperson would be in position to demo our product during their first week or two on the phone. That meant they were likely to forget what they learned about Demoing and Closing before they had a chance to perform these steps.

Based on this “reasonableness test”, we adjusted our baseline viability to be:

  • The rep has a working knowledge of the Inbound Marketing methodology and the best practices necessary to execute various Inbound Marketing strategies
  •  The rep has demonstrated proficiency with all of the tools within the HubSpot software
  • The rep can clearly articulate the business value of various Inbound Marketing strategies and the HubSpot tools that support those strategies
  • The rep has demonstrated proficiency at researching leads and developing compelling springboards into sales conversations
  • The rep has demonstrated proficiency in executing the voicemail/email sequence we use when prospecting
  • The rep has demonstrated proficiency in executing the Connect call process
  • The rep has demonstrated proficiency in executing the Inbound Marketing Assessment call

With this new baseline viability in place, we made two significant changes to the onboarding program. First, we decided to teach the first four steps of the process within new hire sales training and then teach the Demo and Close steps on the job.  I set up a program where our sales people spent 100% of their first month on the job in training.  The second month they spent 75% of their time on the job and 25% in training learning the Demo and Close steps.

onboarding 4

This allowed us to create a challenging training environment that kept new sales hires from becoming overwhelmed, and it also allowed us to keep the things they learned in tight sync with when they would actually apply those skills.

Learn and Do Training Model

The second important change was developing a “learn and do” training model. For each knowledge and skill area, a new rep would learn all the necessary elements in the morning and then put them into practice in the afternoon. For example, our sales people needed to be proficient in the following areas:

  • SEO
    • I would teach them the principles, and then they would build their own web pages on our content system and optimize them to rank on the first page of Google for relevant keywords.
  • How to create and optimize a conversion path for prospects visiting the blog or web site
    • I would teach them the best practices, and they would go build Call-to-Action Buttons, Landing Pages, and Thank You Pages using our tools, and then later present their creations to their classmates.
  • Selling skills
    • I would teach them the HubSpot approach to researching their leads and they would then spend the afternoon researching leads in preparation for outbound calls the next day. On the following day I would teach them the HubSpot approach to using voicemail and email to prospect, and then they would practice by calling my voicemail and sending me the emails for feedback. Finally, I would teach them how to run the Connect call and they would then start dialing the leads they researched trying to get a prospect on the phone to book a Discovery call. (To make the Discovery call more interesting to the customer, we would offer to do a complete Inbound Marketing Assessment for them, so we refer to the discovery call as an Inbound Marketing Assessment, or IMA.)

How did you know if the new onboarding was working?

Training can be notoriously difficult to quantify. We used a mix of assessment methods to validate the knowledge and skill acquisition necessary for success, including:

  1. Project completion
  2. Testing
  3. Practice certifications
  4. On the job evaluation

For Inbound Marketing and product knowledge, every salesperson has to complete a website project during their training month that makes them “feel the pain of a marketer”. They are required to build a blog which ranks on the first page of Google for at least ten keywords, they execute a social marketing strategy using Facebook and Twitter, they secure at least 4 organic inbound links and they set up marketing automation work flows along with a host of other inbound marketing tasks.

In addition, they need to pass a sixty question test. The test is composed of questions like “What are the five best practices for business blogging and why are they important in driving quality traffic?” While these type of open-ended questions take more time to grade, it is an effective way to determine if new sales people can articulate key value points.

New hires also need to pass certifications on the first four steps of our sales process. For the Research step, we inspect the quality of the research conducted and the potential springboards into a sales conversation they developed. For the Prospecting step, we evaluate the voicemail and email sequence they send me during their practice time. For the Connect and Discover step, we evaluate performance through role play. There is a scoring rubric for each of these certifications.

Of course the real indicator is performance on the job, but sales performance is a lagging indicator and thus you need to track each cohort closely.

I pay close attention to each training cohort for their first six months to gauge the effectiveness of the new sales hires’ training program over time and make adjustments as necessary.

Comment on Assessment from David Skok

With the right Assessment tests in place, there is a very high chance that you’ll be able to identify bad hires early in their lifecycle, and remove them fast. In the sales world, being able to do this several months before they fail on the job has significant financial implications. You have a chance to replace the lost productivity of the poor performers with better candidates before they cause you to miss your plan.

If you were advising an entrepreneur on how to create their first sales onboarding course, what would you tell them are the key modules they need to cover?

I would advise the entrepreneur to start by detailing what their new sales hires need to know in the first few weeks on the job to have the optimal foundation to quickly make meaningful contributions. That should include things like:

  • What we do
  • Why we do it
  • What we believe in
  • The culture we have that supports what we do
  • Who our customers are and why they buy from us
  • What they buy from us and why they buy it
  • What they buy from our competitors and why they buy it
  • The tools you will need to do your job
  • The process we use to find prospects that might want to buy what we sell
  • The process we use to help those prospects buy what we sell
  • The process we use to keep our customers over time

Next, I would focus on figuring out what the best way is for a new sales hires to learn all of the information listed above. I find the best way to do that is through backwards planning, as follows:

onboarding 5

Here’s an example:

  • A new sales hire will be able to conduct effective lead research that includes uncovering key decision makers, identifying compelling reasons why the prospect would buy our product, and developing effective springboards to launch a sales conversation with a prospect.
  • This skill will be verified by giving the new hire 5 random prospects that need to be researched to our standard within 30 minutes. The research will be reviewed by a qualified member of the team using a scoring rubric.
  • During the module, the new hires will be partnered up and given several leads to research. They will present back to the class the potential decision makers they uncovered, the compelling reasons to talk, and their springboards.
  • The skill necessary to conduct effective research will be demonstrated by a subject-matter expert. During this time a job aid will be provided and discussion will be facilitated with the class to support the concepts being taught.

I want to be clear here. Not every knowledge and skill area needs to be taught by an instructor.

Backwards planning helps you decide if a certain knowledge or skill area has to be instructor-led or if it can be acquired through self paced learning.

Applying backwards planning to all of the knowledge and skill areas listed above creates the framework for the program. From there, I recommend thinking through the need for a more holistic knowledge check which could take the form of test or a role play that incorporates several of the steps that have been taught.

Who should be involved in developing and presenting course materials?

There are a couple of ways to tackle this. In all of them you need someone who is the Directly Responsible Individual (DRI). While this might not be their full time job, it needs to be something they own and are measured on. Without a DRI it is very hard to maintain a consistent program over time and as you scale it will start to break down.

In the early stages of growth, an effective approach is to have subject matter experts go through the backwards planning exercise for their subject area, develop a module, and deliver the training for that module.

Don’t be surprised to learn that the founder and CEO may be the best subject matter expert on several of the topics.

Once you get to the point where you are hiring three to five people per month that require training, this process typically starts to break down.

At this point, you should consider hiring a dedicated person to develop and run the program.  This person will need to rely on subject matter experts to develop the materials and may need those same experts to co-facilitate training sessions while ramping into the training role. This approach has a higher likelihood of creating a consistent execution of the program over time. But, you need two things to justify this role:

  1. A consistent incoming flow of new hires over a short hiring cycle. I was hired when we started consistently bringing on three sales people a month with the expectation of increasing new-hire volume over time.
  2. A steep learning curve for the new people you are hiring. At HubSpot every new sales person needed to gain working knowledge of Inbound Marketing, learn to use our product and master our sales process. That’s a lot to pick up in a short window of time.

What should entrepreneurs look for in the person who will build their onboarding programs?

There are five characteristics you should look for:

  1. A process oriented, analytical mind. The person should have the ability to break a repeatable process down into its parts and figure out an effective way for others to learn that process.
  2. A lot of patience. You have to have a high degree of patience when working with adults who are learning something new.
  3. A high tolerance for repetition. When you arrive at a scalable process you have to be able to repeatedly train that process with minimal variation from cohort to cohort to ensure consistent outcomes.
  4. A focus on small iterations. Rarely is the first approach the optimal one when working to drive the knowledge and skill acquisition of an adult learner. You need to be able to step back, evaluate and analyze your training approach, and make adjustments that yield the most consistent outcomes.
  5. A flexible nature. Perhaps most important, you can’t be rigid, particularly in a hyper-growth environment. You have to know how to balance flexibility with consistency in order to create a stable onboarding environment for new people joining the organization. You also have to be comfortable with ambiguity. Training is notoriously difficult to measure which can create tension in an intensely metrics-drive organization.

Are there any other lessons that you have learned along the way that you can share?

Yes, here’s an important one. I mentioned patience above when teaching adults, but patience towards the process is also critical. The real indicators of a program’s success lag far behind the execution. Let’s say there is an expectation that a new sales hire has four months to ramp to full productivity. By the time the first cohort has hit the ramp deadline, another three cohorts will have gone through the program. And if each cohort is only three people, that is an extremely small sample size against which to evaluate the program. If two of the three hires fail to meet the ramp requirements you won’t know if it’s because of a flaw in the onboarding program or if you made some bad hires?  If you’re not patient, you might prematurely kill an effective program.

To accurately judge if your program is working, you’re going to need anywhere from six to eight months. That can be hard in a fast-moving environment.

This one is also key. Training debt is painful. Anything you create has to be maintained. In a fast-moving environment the training materials become dated very quickly. That’s another reason why you need a DRI or a full time trainer.  If you don’t have someone overseeing the program, curating the materials and keeping it all in sync with the business as it changes, the program starts to degrade quickly and that adversely affects scaling the key behaviors that drive success.

About Andrew Quinn:

ATQ - Head Shot

Andrew has been involved in professional selling for 28 years working in a variety of selling situations.  The common thread through all of his sales roles is a focus on consultative-transactional selling in short sales cycles of 90 days or less. His first sales job right out of college was selling Bose Acoustic Wave Music Systems direct to consumers (think door to door sales for Kirby Vacuums or Cutco Knives). He then moved to Yellow Pages sales with NYNEX (which became Bell Atlantic and eventually Verizon), spending 16 years across two tours of duty as a sales rep, a market manager, a sales manager and finally a sales trainer. In between his two stints at Yellow Pages, he worked worked for a number of companies including Microsoft and BuyerZone, that were looking to capitalize on the initial internet boom in the late 90’s and early 00’s.  He joined HubSpot in 2009 to develop their initial sales training program. Follow Andrew @andrewtquinn.