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Ask Me Anything About Training and Customer Success With Bill Cushard

Written by Sarah E. Brown

Published on May 29, 2015

As Head of Training at ServiceRocket, Bill has in-the-trenches experience building learning functions in hyper-growth organizations. He specializes in helping customers create long-lasting, loyal relationships between software companies, enterprises and their software by delivering these elements to enable customer success.

In partnership with HubSpot’s Inbound.org, Bill was asked to answer questions about customer training and customer success in a real-time ‘Ask Me Anything’. Here are some of the highlights.

Note: For the full AMA transcript, see the discussion archive on Inbound.org ]

Question: What are the best methods and learning strategies to teach students how to use complex software packages?


First, I would say, do not underestimate the time it will take people to learn complex software. More than once I have proposed training times of many hours to many days and was told by customers or bosses....."No way....that's way too long." Guess what.....people complained they didn't learn or wasn't given sufficient training. As for methods.....labs/hands-on practice is vital. Also, focusing on work tasks instead of features help put the work in context, so it sticks.

Finally I would make sure to start any training like with with why the software was purchased, why it matters to learn it, and what the software can do in general....in other words...put it in context. The people in the training class are not likely to be the people who purchased the software.

Question: What do you think are the top three things that every SaaS company should be doing with the training they provide?


Bill Cushard

1. Focus on work tasks, not features. Help people be better that their jobs. Don't just go through each tab walking through features.

2. More instructor-led training, and less self-paced online. I know it's 2015, but can you really trust that your customer will learn your product watching a video on her iPad while waiting at the dentist? Instructor time is valuable.

3. Offer training tiers. 1. Free (self-paced, online) 2. medium priced (virtual instructor led) and 3. high priced (private onsite training). And price them differently enough to drive the behavior you want.....mostly meaning, driving people to purchase the virtual live training.

Do I think there are others? I do. But those are 3 of the top things I think more SaaS companies should do.

Question: What is your opinion on Certification Programs?  Tests/exams/certificates that assess and recognize particular skill sets?  

Bill Cushard

We have helped customers develop programs like this. The certification debate is a big one. For one customer I worked with, I spent time with one of their subject matter experts....a core contributor to the open-source technology......he was helping me with exam questions and said to me....."Why would anyone take a test on this stuff. I never took a test." The thing is....certifications are not targeted at him (an early adopter). They are targeted at the early majority and late adopters who want to get jobs and build skills for employment are larger companies.That said, I think the secret is defining them well, and making the credential practice. Don't call it a certification if it is a certificate.

There is a very cool service called TrueAbility that I am learning about now. I think they may have cracked the nut when it comes to performance based testing in technology.

Question: What's the best way to hand off a new customer from sales to services for software training?


There needs to be an owner of the customer. I'd say a Customer Success Manager role who joins in late in the sales process and facilitates the customer journey from closed/won deal to on-boarding to training to support to renewal. This CSM role gets the training team involved to schedule training very early on so the customer knows what is happening. The customer has a feeling of confidence in their purchase when this process is organized. I would just add that this involvement with CSM/Training should be earlier than most people think.

Question: What are the 3 things you see companies doing wrong when it comes to training their customers online?


1. Too much focus on feature training

2. Trying to cover everything and not focusing on most important tasks

3. Starting off with free training and trying to make it a paid offering. Companies should start with free and paid training from the start.

Question: My SaaS company decides to invest in training. Now, I'm the first training employee at this SaaS company. Where do I focus my time? What do I build first? Videos, live training, something else?


Check out my eBook on this on building a strategic training business for software.

There is no one answer to this question. I've seen open-source companies start off investing big money in 3-5 day onsite training courses in cities all over the world and I've seen companies only do weekly webinar-style virtual training.

The short answer it is a strategic decision. The worst thing you can do I think is start off offering free training (stamping it as 'no value'). It is hard to start charging for it later.

Think about the continuum of training offerings and then when you might offer it (or whether).

1. Self-paced online

2. Virtual instructor-led (private and public)

3. Onsite (private and public)

Question: In College today many teachers are focused on flipped classrooms, where the students decide what they want to learn and the teachers help them get there. Is there a corollary for online training?


Yes. In fact, Docker is taking a bit of this approach at their conference in June. They are running mini-tutorials on specific use cases throughout the day. Student will be expected to do "pre-work" on their own before attending the tutorials. Their tutorials will not cover concepts but will cover discussions/examples of practical use of the software.

This is huge. And enables a higher value discussion in a training session at a conference. 

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Originally published May 29, 2015 12:25:00 AM, updated Jun 24, 2015