Closing Time

How to Get (and Keep) a Job as VP of Sales

Becoming a first-time VP of Sales is not for the faint of heart.

The successful track record. Tip-top resume. Nailing the interview process.

But as soon as you land that VP title, the hard work has only just begun.

In this episode of Closing Time, we speak with Amy Volas, owner of the Executive Search Firm Avenue Talent Partners, about the biggest struggles VPs of sales and sales executives face throughout their interview process and during their first 90 days on the job.

Watch the video:
Key Moments:
VP of Sales Resume Tips and LinkedIn Prep

As an aspiring first-time VP of Sales candidate, crafting an effective resume and LinkedIn profile is crucial to stand out in the competitive job market. Your digital footprint and resume are your invitations for a conversation, and you want to make a lasting impression. Here are some essential tips to make your profile and resume compelling:

Understand the Purpose: Recognize the primary function of your resume and LinkedIn profile. Your resume is a leave-behind document that should spark interest, while your LinkedIn profile serves as a digital representation of your professional brand.

Embrace Storytelling: Storytelling is a powerful tool to captivate potential employers. Share your growth story, focusing on your journey from an individual contributor to a chief sales officer in just four years. Highlight the challenges you faced, the strategies you employed, and the outcomes you achieved.

Be Precise and Specific: Avoid using generic jargon and hollow bullet points. Instead, be precise and specific in your achievements. Include one or two power statements for each experience, backed with quantifiable results, demonstrating your impact.

Numbers Matter: Incorporate numerical data to showcase your achievements. Include key performance metrics such as revenue growth percentages, sales targets surpassed, or market share gains. Quantifiable results add credibility to your profile.

Focus on the Why: Explain not just what you accomplished but also why it matters. Connect your achievements to the broader impact they had on the company, team, or clients. Show how your contributions made a difference.

Tailor to the Role: Customize your resume and LinkedIn profile for each application. Highlight experiences and skills that align with the requirements of the VP of Sales position you’re pursuing.

Showcase Leadership: Aspiring VPs of Sales should emphasize their leadership abilities. Highlight experiences where you’ve led teams, mentored others, or implemented successful sales strategies.

Highlight Learning Experiences: Share lessons you’ve learned throughout your career journey. Demonstrating a growth mindset and a willingness to adapt and learn can be very appealing to potential employers.

Professional Branding: Ensure consistency in your branding across your resume and LinkedIn profile. Use a professional photo, create an attention-grabbing headline, and write a compelling summary that showcases your unique value proposition.

Networking: Leverage LinkedIn to expand your professional network. Engage with industry peers, share relevant content, and participate in discussions to build meaningful connections and increase your visibility.

Common Interview Questions

When it comes to the interview process, be well-prepared for multiple interviews that may involve various stakeholders, both within the organization and potentially board members. The interview process for such a high-level role is rigorous, and candidates should anticipate questions that delve deep into their past achievements, strategies, and approach to sales leadership.

To prepare effectively, candidates should focus on the following:

Quantify and Qualify Achievements: Be ready to back up any big statements with specific examples and data. Merely stating accomplishments like tripling business without explaining the methods used won’t suffice. Interviewers will likely ask for details, such as how it was achieved, what the plan was, how the playbook was orchestrated, and how often it’s iterated.

Understand the Job Description and Goals: Thoroughly analyze the job description and understand the specific goals and expectations for each aspect of the role. Tailor your responses to align with the needs of the company, its sales challenges, and the desired outcomes.

Be Prepared to Discuss Specific Use Cases: The best preparation involves having multiple use cases to showcase your abilities and experiences. For example, if forecasting is a critical aspect of the job, come prepared with examples of creating a forecast from scratch, fixing a problematic forecast, and your experiences with improving forecasting accuracy.

Ask Relevant Questions: During the interview, be prepared to ask questions that directly relate to the tasks at hand. Demonstrate genuine curiosity about the company, its processes, and the challenges they face. Asking insightful questions shows your interest and thoughtfulness.

Be Ready to Get Granular: While you need to discuss high-level strategies and big-picture concepts, be prepared to dive deep into specific details when asked. Showcase your ability to analyze situations, make decisions, and handle granular aspects of sales management.

Remember that the interview is a two-way street. Just as the company evaluates you, you should assess whether the organization and its team align with your values, work style, and career aspirations. Consider the long-term commitment involved in the role and ensure it’s a good fit for both parties. Demonstrating genuine interest, curiosity, and alignment with the company’s needs will make a strong impression on interviewers. By effectively preparing and being comfortable with the interview process, candidates increase their chances of securing this crucial leadership role.

The First 90 Days as VP of Sales

As a first-time VP of Sales, the initial 90 days on the job are the foundation of your employment at that company – you can either set yourself up for success or failure.

The first 30 days should primarily be focused on listening and immersing oneself in the business. Understanding how the organization operates cross-functionally is essential – from marketing, customer success, product, procurement, accounting, and sales operations. Make plans to meet with each team leader during your first 90 days to establish rapport and emphasize the need for alignment across teams. Listening and building relationships cross-functionally are key.

Evaluating the sales team is equally important. Avoid coming in with an overconfident attitude or forcing a pre-existing playbook onto the team. Meet with each individual on your sales (if possible) and express your interest in understanding their experience, success, satisfaction, goals, and desires at the company. Trust and confidence are earned through these interactions. Assess whether the right people are in the right roles, and be prepared to reshuffle if necessary. To be a credible ambassador for the team, a VP of Sales must know the product inside out, being able to talk about it and demo it effectively. Take the necessary time to watch product demos, review sales demo calls, and enablement material.

You should also focus on understanding the customers. Why do they buy from the company? What makes them stay? Identifying common patterns and themes can uncover opportunities and lead to better decision-making.

Be open to questioning existing processes and ways of doing things. If the response is “we’ve always done it this way,” be cautious, as this might indicate the need for reevaluation and change.

Common Pitfalls of Sales Executives and How to Avoid Them

One major pitfall of first-time VP of Sales is when they solely focus on their own agenda, attempting to force-feed their playbook without considering the existing strategies and processes. Another mistake is isolating themselves from other executives in the team, creating a silo effect that hampers collaboration and unity across departments.

Some new leaders neglect to understand the buyer journey thoroughly and rely solely on information from the sales team, missing out on valuable insights from other departments like marketing, customer success, and product teams. To avoid these errors, it is crucial for sales leaders to listen actively and conduct a time study to truly understand where their team’s time is being spent. This provides valuable data for making informed decisions and identifying recurring themes and challenges.

Building trust with the sales team is vital. Fear and uncertainty can lead team members to withhold information and give superficial responses. A VP of Sales should approach one-on-one meetings with a notebook, actively taking notes and looking for common themes to gain a deeper understanding of their team’s dynamics and individual traits. Having empathy and understanding for the challenges that team members face can foster a cooperative environment and contribute to finding common ground for growth and success.


Imagine you get your dream job as VP of Sales and then you lose it. Let’s talk about ways to avoid that outcome on this episode of Closing Time. Hi, I’m Dave Osborne, Chief Sales Officer at Insightly. And you’re watching Closing Time the show for go-to-market leaders. Today, I’m joined by Amy Volas, strategic advisor for startups in the SaaS space and owner of Avenue Talent Partners. Welcome to the show, Amy. Thank you, Dave. I’m tickled to be here. It’s good to be back.. Thank you for having me. Awesome. Well, Amy, I’m excited for our conversation today. So, I mean, if you want to be a VP of sales and if that’s your dream, this is the episode for you, right? Absolutely.. We’re going to break it all the way down. All right. Well, let’s jump right into it. So if you’re looking for that type of role, head of sales, VP of sales, you’ve got to have a top notch resume, right? And you got to have a strong LinkedIn profile, I would assume. What are some of the other vital elements of the resume, LinkedIn profile game? I think it’s about understanding what those two things do for you before we even dig into what to do with them. So it’s it’s like a footprint digitally speaking or your resume is a leave behind, digitally or otherwise. This is merely an invitation for a conversation and you want to stand out. And so when everybody else is zigging with. I am a revenue leader that has done X and I help companies do this, everybody says the same thing and it’s riddled with jargon and it is a snooze fest. And what people need to realize is if somebody is looking at you for potential employment, they’re spending less than 10 seconds looking at what you’re giving them. If you look like everybody else, my eyes glaze over. So this is where storytelling really becomes front and center as a superpower. Sprinkle me with a little bit that leaves me wanting more. So think of yourself like a Super Bowl commercial. And what I mean by this is you don’t have to tell me every single thing that you did, and you don’t have to take it all the way back to when Dave was in the womb and he came out. This is what happened. And then he went to kindergarten, and then he went to high school and then… no, no, no, nobody needs to know that. But you know what I’m really especially interested in is your growth story. And so if you tell me that you know, you went from being an individual contributor to being a chief sales officer inside of four years,. I’m really turned on by that. You had to do a lot of things to get there. That’s going to automatically mean. I want to know more, how did you do it? Why did you do that? So sprinkle me with some of these statements. So what I mean by the Super Bowl commercial is, think about the Super Bowl. You have a very short amount of time to pack a very big punch. What did you do? Who did you do it with? Why did you do it? What were the lessons that you learned? What were the outcomes?. And put numbers to it. And so what? Why does it matter, not to you, but to somebody else? And if you can have one, or one and a half two power statements to each thing that’s now you weaving the fabric for what you put externally on your resume or on that LinkedIn profile and back it out from there, because now you’re specific, you’re precise you’re not using jargon, you’re telling your own story, and that’s magnetic. That’s the story of you not trying to talk about you in the same way that everybody else does. No, I love that. Thanks, Amy. I can’t tell you how many resumes or profiles I see that are just riddled with hollow bullet points. Right. But I think you’re exactly right. The ones that can weave it or tell a story, right is so much more compelling. So I think there’s some great advice. OK, so we’re going to have multiple interviews, obviously, with many different stakeholders, both within the organization and potentially board members. What types of questions should VP sales candidates expect to be asked and what’s the best way for them to prepare? So the best way for them to prepare is to know exactly what they’ve done, what they do well, what they want to be doing, and to be able to back that up to quantify and qualify their big statements. So the number one reason why a VP of Sales doesn’t get through in my process or with my clients, they can’t get specific. They make really big statements like I tripled the business well, how did you do that? So I hired a bunch of people. OK, what was your plan? Well, I have a playbook, like, see how it’s like pulling teeth and it’s like what’s in your playbook? How did you orchestrate your playbook? Why did you create your playbook? How often do you iterate your playbook? What are the factors, you know, like how did you put those dots together? It’s that kind of stuff that’s really missing. So when you are preparing for a role, one of my best tricks that I tell people is get the job description and each and every step understand what their goal is for that. So in my meeting with Dave and Chip at the same time, so Dave heads up sales and Chip heads up marketing what would they like to get out of this? And then I’m going to listen and I’m going to make notes. And based on those notes of how you’re telling me what to expect, I’m going to come to the party really well prepared of, so Dave really cares about my ability to forecast. OK, so I’m going to talk about when I’ve had to create a forecast from scratch, and I’m going to talk about when I inherited a forecast that was horrible and it was the worst thing since sliced bread because we couldn’t forecast the business because it was terrible and how I stepped in to fix it and then I’m going to talk about when I was the person that had a forecast and made all the mistakes when I was early on in my career and what I learned from that so I’ve got now three different use cases of a forecast that’s going to make me really magnetic to you because A, I started out and I learned and I got better for it. B, I’ve inherited a forecast where I had to fix it. These are the things that I did and how the business got better as a result of it. And C, here’s how I can create one from scratch. Which one do you need? So that’s the preparation in terms of the questions. Ask questions or be prepared for questions that are mapping back to the task at hand. And so what is the job? If the job is a turnaround, you’re going to have questions about how you’ve done that before. If the job is a brand new build, you’re going to have questions about how you’ve done that before. And the questions that you should be asking, I’m not going to tell you about that either because the best leaders, they’re super curious about what makes you tick and it’s OK if you get stage fright or you freeze up. Lots of people do. My best trick for that is make notes during the interview, and if it’s on Zoom, have that digital body language to say, Dave, you know what,. I hope you don’t mind. You’ve got my undivided attention. I promise you, I’m not on Twitter. I’m actually making notes over here because I’m listening to what you’re saying and. I want to make sure I don’t miss anything. So when you’re telling me something, Dave, and it’s interesting to me and I want to drill in and I don’t want to be rude and interrupt you, I’m going to make note of that. So when you say, what do you think? I can say, you know what, Dave? You were talking about forecasting and you said that you use spreadsheets. I’d like to better understand why it’s just spreadsheets. Because you also use (Insightly). What’s the difference there? And then you might say to me, well, we’ve never had a sales ops person. And then, you know, see how that’s now we’re actually talking about something real. So prepare to get granular. I think coming right back to like the resume LinkedIn profile, right we got to be prepared to talk high level big picture stuff, but very specific items. You know, we got to be ready to go two, three, four layers deep right. And you know, I think another thing to consider here is like interviewing in a way it’s kind of like dating, right? We’re trying to see if I’m a good fit for you and you’re a good fit for me. And so I think that’s another thing that maybe if you get nervous, you have to kind of imagine is you got to understand that as a VP of sales, you’re going to be getting in the trenches with that other person every single day going forward for a lot of hours a week. Right.. For hopefully months and years on end. So you’ve got to make sure that you’re comfortable with what you’re getting into and the people that you’re doing it with. So I think that’s that’s great. So let’s say everything went well. You got the job right. Congratulations. Awesome. Now the work begins. So what should the first 90 days look like in chair as the VP of sales. So it’s a book that we give to every VP of sales that we place. It’s called. The First 90 Days. Read that book. There we go. There we go. Good little plug. I like that. I didn’t write the book, but it’s a really great book to read. But that first 90 days, the first 30 in my opinion, is all about listening really entrenching yourself into the business of how do we do business? What are our rules of engagement? Cross-functionally around the organization? Well, what does Chip do in marketing and what does our customer success team do and what does our product team do and what does our procurement team do and what does our accounting team do and what does sales operations do? And what I mean, and maybe you have some of these functions and maybe you don’t, but it’s really understanding all of that. And also, what is my team doing? Do I have the right people doing the right work in the right roles? Do I need to potentially reshuffle that? I don’t know if I don’t find out. And also who is my customer? Can I actually talk about my product? Can I demo it if I have to? If I can’t do that, how in the world can I be a good ambassador for my team? And if you don’t understand the customer, why did they buy from us? Why do they stay from us? Are there common themes and patterns around who is getting the biggest bang for their buck from us? Is it market driven is it geography driven? Is it some sort of segment that we need to think about? You don’t know unless you find out. And if you rely on your assumptions you’re going to leave a lot of opportunity behind and make some really big mistakes that are really hard to walk back. If you come in super strong of in the first two weeks, I’m going to grin at everybody and think I have all the answers. The news is, you don’t have all the answers. And so if you come in and three weeks later you just force feed your playbook because this is how I’ve always done it and this is what we do, you’re going to have some huge misses. You’re going to turn a lot of people off. You’re going to make life a lot harder for you. And chances are you’re probably going to be that statistic that churns within 16 to 24 months as a sales leader. It’s great advice, I think coming in with the listening philosophy is really key, right? I mean, coming back to our earlier comments as a sales leader, you got to be building relationships cross-functionally right? So as you meet with different individuals, get to know them, hopefully start to build that trust and confidence and then getting that lay of the land, right? Like what’s going well? What are the things that we should continue to invest and build on? What are things that are not going well or points of friction that we can focus on for the next few weeks? Or months? I think another common thing that people would think about here is that here is, why are we doing this process or this thing this way? And when someone says, well, we’ve always done it this way, that should be a huge red flag, right? Because in some ways what got us here isn’t going to be what gets us to where we need to go. So kind of be open to reevaluating so many different things. So we’ve heard what to do.. Curious about what not to do. What are some typical pitfalls that new leaders make on the first six months on the job? They only focus on their agenda. So we talked a little bit about that where it’s like, here’s my playbook and I’m just going to force feed it in. They don’t spend time with any of the other executives on the team, and then they’re creating a silo effect, right? So what doesn’t work is sales against the world. That’s just not just not good. They don’t spend any time understanding the buyer journey and they just rely upon what the sales team is telling them. And that’s not the way to do this. Because here’s the thing. If you own the whole go-to-market strategy, how in the world are you going to be able to be an advocate for the buyer journey with the product team, with the marketing team, with the CS team, with anybody else for that matter? So I look at it as the pieces of the puzzle. So it goes back to what we’re talking about with that listening piece. And the one thing just to go back to what we talked about that’s super actionable. I love that you brought up our our friend Marshall Goldsmith, that wrote a lovely book about what got you here, won’t get you there. Totally true, but a great thing to do as a leader that helps you understand what to do and what not to do is to do a time study, walking through the door, for yourself and for the entire team. Where are people spending their time? Because what are perception is is not necessarily reality, especially when you’re spending one on one time with the team. Any leader that walks through the door, it is natural human, just like it’s part of being a human to be scared. This leaders coming through, is my job OK? Are they going to change everything? Is my life going to get harder? Is this person a total jerk? Are they going to be a micromanaging maniac? Like what am I getting into here? They’re afraid of you whether they say it or not, they are. And when people are afraid, they don’t open up like a blossoming flower to you. They’re only going to tell you what they think you want to hear. That makes them look good. And so trust is one of those things that’s earned over time. Just because you had a good one on one and it felt good. Doesn’t mean that you’ve earned that trust or that respect or that they’re telling you all of the things. That’s why I like a time study. So now that you actually have some data to do something with. So one of the things not to do is to assume that what you’re hearing that you should take it for face value. You should not and you should actually show up to those one on ones, especially with your team, with a notebook and make notes and look for the common themes week over week. So Dave, last week you told me that you’re really struggling with this deal.. This week, we haven’t talked about that deal at all. And now we’re talking about this other thing over here. What happened with that deal? Now, Dave, you feel like I’m hearing you and we’re cooking with gas and that big thing from last week isn’t that big of a deal at all. And now I’m learning that Dave actually is a total normal salesperson that gets wigged out at the 11th hour that thinks that they’re not going to close anything and it actually closes. But they have that weird superstition part. OK, I know this about Dave, and I can actually be there for Dave in that moment to talk. Dave off of the ledge because of that. Got it. See how I’m not assuming. I’m actually using that data. That’s great, great, great call outs. And especially with, you know, building that trust relationships right it’s you know, it takes a while to dig in and start to establish those that level of trust and confidence. So I think great, great counsel. I think as a VP of sales, you’re coming in trying to get your understanding the lay of the land, trying to get to know your people. But I think having empathy with the person on the other end of that desk or the other end of that phone is an exact same place. So we’ve got to work together to hopefully find that common ground. Amy, really grateful to have you on the show today. Thank you so much for having me. I hope this was helpful for anybody that joined us. Remember, if you like this video, subscribe to the channel, tick that bell for notifications so you don’t miss an episode. We’ll see you next time on Closing Time.

You may also like:

See all episodes
Amy Volas thumbnail
How to Build a Competitive Sales Compensation Plan in a Volatile Market
How to Build an Effective SDR or BDR Team (Sales & Business Development Representative)
Best Practices for Creating and Maintaining a Winning Sales Territory Plan