How to Nail your SaaS Role-play Interview

Two years ago I had to do my first sales role-play when interviewing for my first SaaS job at Clio. This was a huge deal to me as I knew I wanted to get into SaaS, and I needed someone to take a chance on a sales guy whose professional experience consisted primarily of hocking office supplies to receptionists. 

My interviewer was Steven Silberbach, who had spent over 8 years at Salesforce seeing literally thousands of role-plays over that time span. I had never done a case study role-play before and was more than a little intimidated, so naturally, I googled it. Unfortunately, there was no guide to be found. I put a lot of time into planning for every possible contingency and objection and ultimately that work paid off.

Since that time, I crushed another role-play to earn a highly coveted Account Executive job at LinkedIn, returned to Clio to lead the SDR team and now find myself sitting on the other side of the table, evaluating talent based on the quality of their role-plays.

This guide represents the most important things I have learned about role-playing interviews in the last 2 years. Hopefully, it can save you some time and help you land your dream job.

Context

The role-play is typically the final interview round and the one that really separates the professional interviewers from the strong, agile salespeople that, as hiring managers, we all covet.

For this interview, you will be given a case study to review and use as a starting point. This will likely contain some information about challenges that the prospect is experiencing and/or business objectives they are hoping to achieve. You may also be given the freedom to determine the challenges the prospects face.

There will likely be multiple interviewers taking part in the role-play. The information you’ve received has generally come from meeting with the various players.

A small disclaimer. The language used here may seem a little too on the nose. My goal is to outline the logic that your role-play should follow. Make sure that your tone and language is yours and more importantly, sounds conversational.

Finally, you MUST reach out to your interviewer(s) in advance. Not reaching out with questions indicates that you either don’t care or don’t think you need any coaching.

Make a game plan as soon as you get the case study. Read it several times and be clear on what the interviewers expect from you. This guide should help. Next, reach out to ask any questions that you have, and confirm that your approach is a good one. Give yourself enough time to make adjustments if they give you indications that you aren’t on the right track.

How to structure your interview

1 - Greetings/Introductions

Greet everyone in the room. If there are people there that you have not met with yet according to the case study do introductions. You need to know who all the players are.

2 - Agenda

Establish the Agenda for the meeting. A good one might sound something like this.

You: I’ve put together an agenda, let me know if this works for everyone or if there’s anything we need to adjust.

I’d like to start by confirming what I’ve learned from the conversations that I’ve had with each of you so far and make sure we’re all on the same page as far as what you’re hoping to achieve.

Then I’d like to go into a bit of detail about how our solution can help you address those priorities.

Finally, based on that we can determine the appropriate next steps. Does that work everyone?

3 - Confirm what you’ve learned

Here you want to go point by point through the key objectives and challenges that the prospect is hoping to solve for.

Clearly articulate the crux of the challenge to the person who told it to you and get them to elaborate on it. In a perfect world, you want to get them to quantify the challenge in terms of time or money.

Once they’ve done that, confirm with the rest of the players that they see the challenge the same way and are in agreement about what it would mean to solve the problem.

You: Karen, you told me that there is a concern that your sales reps are spending too much time on administrative tasks when you would prefer they be spending more time on the phones. How much selling time do you think is being lost to admin work?

Karen: Reps are probably losing, at least, an hour a day to administrative tasks that I think we could probably be automating.

You: Thanks, Karen. What kinds of tasks are those?

Karen: There’s a lot of duplicated effort between various systems and logging everything into our CRM, rewriting the same emails over and over, repetitive voicemails. Stuff like that.

You: John, does this sound about right to you?

John: Yes

You: How much more do you think your reps could be selling if you could get them that hour back?

John: It’s hard to say.

You: Well 1 hour a day is about 13 percent of the day. Let’s say conservatively that they can increase sales by 5%. Is that fair?

John: Yes, that’s fair.

You: OK great. And from my conversation with Sarah I understand that your reps on average produced $1m in revenue last year and that you have 10 reps. So you could potentially be increasing revenues by $500K if you’re able to automate this admin work then?

Sarah: oh. Wow. Yeah, I guess that’s right.

You: Karen?

Karen: Yes, those numbers make sense.

You: OK, it sounds like giving them that hour back is a major priority then?

John: It is now.

Then rinse and repeat for each pain point/business objective. Finish with:

You: Is there anything else I’ve missed? Any additional concerns or challenges that we haven't discussed?

If yes, handle them the same as the others. If not, you are ready to move on.

4 - How you cure their pain

If you’ve done everything well up until this point you’ve got 2-3 really great pain points and the players have agreed that solving them is a priority.

Now you want to go through those pain points and articulate clearly and concisely how your solution will address those concerns. Next, gain agreement from the players that they believe your solution actually solves for the challenge.

You: All right. What I’d like to do now is share how our solution can help you address those challenges. Is that ok?

Sarah: Sure.

You: Great. So we established that reps are losing, at least, an hour of their days to administrative tasks and that that is costing you $500K in lost revenue.

We can automate the majority of those admin tasks through our sync with your CRM, phone and email systems.

Calls and emails will automatically log to your CRM. Additionally, your reps will be able to send templated emails that auto-populate. Finally, they will also be able to pre-record voicemails and leave them with just one click.

Do you think this will allow you to give your reps that hour back?

John: Yes.

You: Karen? Sarah?

Both: Yes.

You: Ok, that’s awesome. Next, we determined that ….

Rinse and repeat.

5 - Close on next steps

At this point, if things have gone well, you will have determined the key pain points, the impact of those pain points, and finally, you have gained agreement that your solution will successfully address those concerns. The only thing left is to ask for the appropriate next step (asking for the business, a product demo etc.) This should sound something like this.

You: Perfect. So based on everything that we’ve discussed here it sounds like our solution is a really great fit. Is there anything else we need to address before moving forward?

Here you are likely to see some objections or buyers that are looking to move forward, but not in the way you had hoped. Perhaps they want to pay a lower price or go with fewer users or a less expensive package. Be calm and bring it back to the value your solution is going to provide. If you did a good job of getting them to quantify this should be easy.

You: Karen, I appreciate your concern around pricing. I’m curious, though, we spoke about the time it’s going to save your reps and how they could collectively generate another $500K in revenue, and the solution only costs $100K. What am I missing?

You should be prepared for as many “standard” objections as possible. Remember you’re only getting one shot at this.

Still they will inevitably throw something at you that you didn’t or couldn’t prepare for. I won’t go into objection handling technique here because it’s a topic unto itself, but resist the urge to speak immediately and give yourself a second to think. This will help avoid rambling.

Once you’ve successfully removed the objection (hint: they need to agree that it’s been removed) close on the next step again.

Common mistakes

• Asking broad questions unrelated to the information contained in the case study. Stay on point!
• Assuming that there is agreement amongst the players with respect to the challenges and objectives.
• Giving a general overview of the software, especially at the beginning - If it’s not related to the specific pains and objectives don’t talk about it.
• Pitching rather than asking good questions
• Not being prepared - you should know more or less everything on the company’s website
• Rambling - Give yourself a second to think before responding to direct questions

Final Thoughts

In reality, your role-play is unlikely to go this smoothly. There will be things that you didn’t anticipate and the other players will try to get you off your game and off script. When that happens, keep your composure, handle the errant question or comment and then get back on track. You still have to get through the pain points, articulate how you can solve for them, gain agreement that it solves them, and get a commitment to move forward.

I hope this guide has been helpful to you. I’d really love to read any feedback you have in the comments section whether this has helped you, wasted your time, or worse, blown your one chance at your dream job and true, everlasting happiness. Please share, like, borrow and plagiarize as you see fit.

Also, feel free to add me on LinkedIn.