SaaSX Interview Questions

	A	B
1	Interview question	Considerations/what to look for

2	What questions do you have for me about [the company] and/or the sales organization?	I always start with this question for any sales interview, at any level. I want to know what's important to the candidate, how curious they are, and what their level of business acumen is. If the first interview I have with a candidate is just me answering their questions, that's perfectly OK. I can't stress enough how important curiousity and business acumen is, and how much a candidate's questions reveal about themselves. I am looking for questions about our company, our product, our buyer, our metrics, our culture, our sales cycle, our sales process, and much more.
3	What makes a great sales leader?	This question is more of an ice-breaker than anything else, but it does reveal what their view of leadership is and what they see as the most important characteristics of sales leaderhship are.
4	Your first 30/60/90 days. What do you focus on, what do you accomplish?	I've written a detailed article about what I am looking for in this response. The main thing: Detail, specificity and a focus on the most important things.
5	^ Probe for detail.	However a candidate answers the 30/60/90 question, it probably wasn't detailed enough to satisfy me. Probe for more specificity.
6	What kind of sales leader are you? How would you describe your leadership style?	I like to know how the candidate describes their leadership style. Look for key words in their response and as the interview process progresses listen to make sure their answers align to those key words. Also, this is always an interesting question to ask a few moments after you ask what makes a great sales leader! How do the responses align and if there are gaps between the two answers can make for some interesting follow up questions.
7	How would you describe the ideal sales culture? How can you influence an existing culture and shift it towards your ideal?	A candidate who can't articulate a sales culture is a bit of a red flag to me. It can denote someone who hasn't really led or shaped a team before. It can also reveal if a candidate doesn't value building a deliberate culture.
8	Largest team/smallest team built or managed?	Helps determine their leadership and management experience.
9	Probe to understand their role in building and managing, as they are two different things.	Building and managing are two different things, and the skills don't always translate. Understand your candidate's actual experience and seek to determine if it aligns with what you need. If you need to build a team, someone who managed an existing team may not be able to do that for you.
10	How do you approach territory creation? What do you consider? What do you need to know before you can design territory?	This question is designed to understand their general philosophy on setting territories and territory management as well as reveal their experience in territory creation. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours.
11	Describe your general approach to setting quotas.	This question is designed to understand their general philosophy on setting quota as well as reveal their experience in quota creation. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Also look for detail—do they really understand the business metrics that drive quota setting?
12	What about in cases where there is little to go on? Such as in a startup or an environment where there are limited benchmarks?	I use this question to help determine if the person is authentic. No one has a magic formula for startup quota setting. The best response is based on evaluating industry benchmarks, setting quarterly quotas rather than annual until benchmarks are established, and a good dose of "I guess". I look for someone who is trying to BS their answer, versus someone who is just genuine about how many unknowns there are in startup quota setting.
13	Describe how you determine OTE for your team, what factors do you take into consideration?
14	In your opinion should sales or customer success own expansion? Why or why not.	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Also look for detailed reasoning to back up their response.
15	What should customer success be responsible for if the sales team owns expansion?
16	Should sales or customer success own renewals? Why or why not.	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Also look for detailed reasoning to back up their response.
17	If I ran into your last manager on the street and asked them about you what would they say were your weaknesses? Strengths?	I prefer asking this question instead of the over-used "tell me your strengths and weaknesses". Candidates are typically less guarded and more specific when you ask the question this way. I find they often say things about themselves they wouldn't say otherwise.
18	Can you tell me about a time you made a strategic or tactical mistake at work and how you handled it? What was the outcome? In hindsight what would you have done differently?	First, I am looking for humility. Second, I am looking for an actual mistake (no matter how small or large). A candidate who can't provide a real example of a mistake may have an ego problem, may have a self-reflection problem, may be too insecure to reveal or face a mistake, or may just be generally inauthentic. I want a real answer about a real mistake.
19	What are you most proud of professionally?	Shows what they value and where their focus is.
20	Whar sales metrics do you look at daily? Weekly? Monthly?	Shows the level they are used to working within their sales organization. Are they metrics-first? Do they dive deep into metrics or just look at a few leading indicators? There isn't necessarily a right or wrong answer for this, but it helps to get to know their style and sales leadership acumen.
21	If I asked you to create a sales report for a board meeting what would you include?
22	What is your preferred tech stack?
23	Probe for their level of familiarity and proficiency in the tech stack. Are they hands off or do they roll up their sleeves and get into the tools themselves?	The answer you want is stage-specific. Consider if you need someone who has built a sales stack, or someone who has just run an existing sales stack, or someone who is most comfortable having sales ops set up and run the sales stack. If this is your first sales leader and there is minimal internal sales ops support, you need a leader who isn't afraid of running the sales stack themselves for awhile. Someone who has never done that may not be right for your stage.
24	In your opinion does outbound work?	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Also look for detailed reasoning to back up their response.
25	How would you approach building an outbound program from the ground up?
26	What is a sales playbook in your own definition? Do you use one? How do you leverage it? How important is it?
27	How do you organize your department (what does your ideal org chart look like)?	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Also look for detailed reasoning to back up their response.
28	How do you structure your pipeline review meetings? How often do you conduct them?	This will provide insight into their sales management experience and style.
29	Would you describe your decision-making style as based more on "gut", or on "data"?	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours.
30	Describe in detail what a typical day is like for a sales leader?	This will provide insight into their sales management experience and personal work style as well. Probe for specificity—someone who clearly knows the role and job can speak in great detail.
31	What is it like for your reps to interact with you?	This will provide insight into their sales management experience and style.
32	Are you formal or informal? Meeting-driven or open door? Hands off or hands on?	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours. Look for a good cultural fit with you and your leadership team.
33	What is your typical team and individual meeting cadence?	This will provide insight into their sales management experience and style.
34	In your view, what is the difference between leading, managing, coaching and mentoring?	There isn't a right or wrong answer for this. Look for a response that aligns with your philosophy, and/or adds value/perspective to yours.
35	What are the fundamental metrics for any SaaS business?
36	Is there anything unique about selling SaaS that is different from other sales environments?
37	Describe your hiring process.	Look for answers that show they understand the value of a repeatable, rigourous hiring process. Look for experience finding and landing great talent. Do they have people in their network they would bring in immediately?
38	Describe your general approach for managing your A+ players?	This will provide insight into their sales management experience and style.
39	Describe how you manage an A player who is hard to work with/bad culture fit/not a team player?	This will provide insight into their sales management experience and style. Ask for specific examples.
40	What will you tolerate from that type of sales rep, and what won't you tolerate?	This will provide insight into their sales management experience and style. Ask for specific examples.
41	How do you coach/manage reps who are underperforming?	This will provide insight into their sales management experience and style. Ask for specific examples.
42	How do you know when you need to let a rep go? What process do you follow once you have made that decision?	This will provide insight into their sales management experience and style. Ask for specific examples.
43	Describe the rep who was the most difficult to manage in your career so far?
44	Let's say you have a sales rep who is always a top performer consistently every quarter. You discover that her/his emails are littered with typos, bad grammar, and incoherent sentence structure. What do you do?
45	What if what you described wasn't effective, and you didn't see improvement?
46	Let's say you come in to manage a team and determine that one of the first things you need to improve is forecast accuracy. How do you go about that?	This is a great situational question to see how they go about setting a course for process change within an existing team.
47	What if it doesn't work? Forecasts continue to be inaccurate after several months—the team is professional and engaged, but non-compliant with your process, they don't update their deals, they don't accurately follow the sales process, etc. What do you do?	This is designed to be a 'challenge' question—by not accepting the response at face value it forces the candidate to dig deeper and shows you how they think on their feet in the face of a difficult question.
48	How do you coach/manage a top performing rep who indicates they want to go into sales management?	I am looking for a nuanced answer that shows they have either had those types of conversations with members of their teams, or they would know how to approach it if they did in the future. Excelling in sales and sales management are two different things, and if a rep wants to move into management there is a lot to consider, discuss and plan for to even determine if that's the right path and then to determine how to help the rep get there if it is the right path. I look for specificity in their response.
49	How do you manage conflict between peers?	Can reveal more about their actual management experience, and their approach to running a team.
50	Have you ever had a situation where you had a conflict with a peer? What happened? How did you handle it? What was the outcome?	A sales leader will be interacting with many parts of the organization—product, engineering, customer success, operations. There is bound to be some form of disagreement or mis-alignment at some point and it's good to hear how they characterize that.
51	What OTE are you looking for? What mix of base and variable?	Even though the question is the last on the list, I usually ask this much earlier—usually at the phone screen or first interview. You don't want to spend lots of time falling in love with your dream candidate only to find they are well outside of your budget. If you don't really have a 'budget' then knowing their target compensation early can give you time to figure out how to create a compensation plan that gets them there.
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