Closing Time

Why Sales Leaders Fail: The Full Business Picture and How to Ensure Success

Sales leaders often enter a new company and start working on their team immediately – restructuring, training, processes, expectations, etc.

This is important, but they are missing the larger picture, which can result in the “sales against the world” mentality.

The best sales leaders do the work early and often to understand how the entire business works before implementing their playbooks.

Amy Volas discusses why sales leaders fail, what pitfalls to avoid, and how they can set themselves up for long-term success in a fresh role.

Watch the video:
Key Moments:
Accepting a New Sales Leadership Role

Switching jobs as a sales leader is no casual walk in the park. Whether you’re climbing the ladder internally or entering a new company as a leader, a successful transition requires a clear understanding of the unique challenges and expectations of the role, proactive communication, and a continuous commitment to delivering results and adapting to the evolving demands of the position. 

At Avenue Talent Partners, Amy and her team specialize in placing executive sales leaders in early-stage startups. One recurring theme is the misconception that landing the job is the finish line. In reality, it’s just the beginning. 

The moment you step into that executive seat, the real work begins. Whether you’re a CMO, VP of Sales, or VP of Customer Success, success hinges on your conduct from day one. And in most cases, it even starts before your first day. 

Believe it or not, how you communicate your excitement and intentions when accepting the role matters. Maybe you have a few weeks between roles – share your vacation plans with your new hiring manager and a few things you’re excited to dig into with them when you start. Being self-aware and setting expectations matter. Thank the hiring manager for grace while you transition between roles. Connect with your new team on LinkedIn; consider messaging a few of them. Letting others know you’re offline but thrilled to get started builds anticipation.

These microforms of communication will set a foundation built on transparency and openness with your new team, and reiterate that you’re the right fit for the job. Remember, the job isn’t just about getting the title; it’s about how you perform in that seat.

Promoted to Sales Leadership Within Your Current Company

Let’s set the stage: you’re an enterprise account executive going on your fifth year with the company. Months ago, you planted the seed about your ambitions for moving into a leadership role one day. When that opportunity presents itself, you take it. You’re now gearing up to transition into your new New Business Sales Manager role at the company.

Amy shares advice for those in a similar situation:

When you get promoted from within the company, you have some advantages – you know the people, the business, and (hopefully) the product.

But here’s the trap: don’t let familiarity lead to complacency. Just because it’s familiar doesn’t mean you can ease up. Especially if you’re in an early-stage company where there’s no one more experienced in sales above you.

If you’re reporting to a founder with little sales expertise, it’s like the blind leading the blind. You’ll face challenges you’ve never seen before. You must be resilient, find blind spots, learn from failures, and adapt fast. Your founder won’t have all the answers, so you need to be prepared to figure things out solo.

Being a top salesperson doesn’t guarantee you’ll be a great manager. Sales organizations often rely on their best salespeople to add their magic to the team, but it’s not always that simple. Moving from an individual contributor to a leader is a big shift. So, think twice before making this move, especially in early-stage companies.

As you move up the ranks, remember that leadership isn’t just about what you want – it’s about your entire team and working seamlessly with other departments. In leadership, you need to play nice in the sandbox, even if you don’t always agree. The CEO conducts the orchestra, but every department is an instrument, making the company’s music. You must fit into this overall puzzle and collaborate effectively.

Hired into Sales Leadership at a New Company

When you join a new company in a sales leadership role, you’re essentially starting from scratch. You need to familiarize yourself with the ins and outs of the business. This includes getting to know the product or service you’ll be selling, understanding your target customers, and identifying the specific problems your offerings solve.

However, this learning curve can be especially steep if you’re entering an industry you’re not familiar with. In the world of software as a service (SaaS) or any other field, gaining this foundational knowledge is essential to effectively lead your team and drive results.

Your team is your greatest asset, and it’s essential to understand their dynamics and capabilities from day one. Identify your top performers, those who are struggling, and everyone in between. This early assessment helps you make informed decisions and tailor your leadership approach to the unique needs and strengths of your team members.

Effective time management is also critical when you’re stepping into a new leadership role. As soon as you walk through the doors, you’ll find yourself pulled in multiple directions. On one hand, you need to actively listen to your team, understand their challenges, and build rapport. On the other hand, you must dive into the company’s internal processes and operational intricacies. Balancing these priorities requires careful time management and prioritization skills.

Listening is your superpower as a new sales leader. Take the time to hear what’s happening within your team and the organization as a whole. Understand the day-to-day challenges your team faces and what keeps them up at night. Building strong relationships begins with active listening.

One common pitfall is the temptation to impose your playbook from previous experiences onto your new team and company. Remember that every organization is unique, and what worked in one place may not apply in another. Think of your playbook as a tool kit—it contains strategies and tactics you’ve mastered over time. However, it’s not a one-size-fits-all solution. Just like remodeling a house, you may open up a metaphorical wall only to find that your tool kit doesn’t quite apply to the situation. Flexibility and openness to new approaches are essential. If the shoe doesn’t fit, don’t force it!

Markers of Great Sales Leadership

As a sales leader, it’s vital to gauge your performance and ensure you’re on the right track. Here are some key markers that indicate you’re doing a good job in your new leadership role:

1. Set Expectations Early: Start by setting clear expectations with your executive team, especially your founder or CEO. Establish mutual agreement on milestones for the first 30, 60, and 90 days. These milestones shouldn’t be a mere formality; they should reflect what you genuinely intend to achieve.

2. Regular Check-Ins: Maintain a consistent communication cadence, whether it’s weekly or biweekly, with your leadership team. Use these check-ins to discuss progress and ensure alignment. Avoid the common pitfall of waiting until the end of a quarter to address issues.

3. Course Correction: If you notice deviations from the agreed-upon milestones, don’t wait until it’s too late to address them. Early detection allows for course corrections and prevents misunderstandings that can lead to turnover.

4. Collaboration is Key: Be wary of red flags like team members insisting on doing things their way without communication. Sales leadership is a collaborative effort, and decisions have ripple effects on various aspects of the business.

5. Alignment in Interviews: Before accepting an offer, discuss and align on expectations to avoid surprises on your first day. This proactive approach ensures a smoother onboarding experience.


In the ever-evolving landscape of sales leadership, it’s essential to remember that success isn’t solely defined by your past experiences but by your ability to adapt, collaborate, and communicate effectively.

Embrace the challenges, set the tone, and lead with confidence, for the journey may have its bumps, but it’s the harmony you create that truly defines your leadership legacy.


So you’re a new sales leader, that’s great.
But beware of some common pitfalls you’ll want to watch out for.
We’re covering that in this episode of Closing Time.
Hi my name is Chip House.
I’m CMO at Insightly.
And welcome to Closing Time, the show for go-to-market leaders.
Today, I’m super excited to be joined by Amy Volas.
She is a strategic advisor to a number of different companies,
especially those in the early stage.
She’s also founder of Avenue Talent. Partners and host of Thursday Night Sales.
Welcome, Amy.. Thank you for having me, Chip.
It’s good to be back.
Lovely to see you.. Got a lot to talk about.
We do have a ton to talk about and it’s great to have you back.
So clearly, if you’re a new sales leader, right,
there’s a number of potential things you need to watch out for
but it’s different probably when you come up in an organization versus
starting out as a, you know, high level leader in an organization.
You know, I can certainly relate to that.
I came in as a CMO here
at Insightly, and certainly. I’ve worked my way up historically.
But marketing is a different animal than sales.
So talk about the sales side of that.
So at Avenue Talent Partners, we place
executive sales leaders with earlier stage start ups, VP of Sales
and VP of CS, and this is a common
thread of a conversation. I have pretty much every single day
where it’s like it’s one thing
to be given the seat at the table that’s called getting the job.
It’s a whole other ball of wax to step through the door
and to continue to get it.
And I think that’s the intersection, like that.
The minute that you walk through that door, just because you
you got the job, the party is just getting started, Chip.
You and I both know this and CMO is not very different
than the sales side, than the product side than any other side.
When you get that executive seat,
it’s all about how you conduct yourself in that seat.
And that starts on day one.
It actually starts before day one,
if I’m being honest.. It starts with, when you accept the role.
How are you communicating your excitement about that?
How are you already starting to think, even if you haven’t resigned yet,
or you’ve resigned and you’ve taken a vacation,
are you leaving breadcrumbs behind to reinforce
that you’re excited, even if you need a much needed break?
Hey, you’re self-aware.
You’re setting expectations around the Hey, I’m offline,
but I’m so excited to get started
and thank you for the grace of understanding that I need this time off.
These are the three things that I’m geeked out to dig into with you.
It’s that piece that reestablishes
the fact that you were the right person for the job, that you’re
excited, that you’re ready to dig in and you’re already thinking about it.
So starts before, and then it starts the day that you walk in.
And it’s reinforced by every action, every decision
every email, every Slack,
every text, every word that you speak.
So I want to talk through both scenarios, Amy.
So let’s first talk about
when you’re promoted in from inside of the company, right?
And so you’re going to know the other people inside the company.
You’re going to have some familiarity hopefully with the business.
You know, since you’ve been promoted, you probably know the product pretty well,
you know the other departments pretty well.
You have some relationship with the marketing team.
So talk about that scenario.
Sort of the new sales leader from within the org.
I find that when you’re getting promoted internally,
one of the risk factors there is that
there’s a little bit of entitlement or I got the job, this is familiar to me.
I can take my foot off the gas a little bit.
And the answer to that is absolute not.
Also, if it’s an earlier stage company and this is a stretch role
and there isn’t really anybody above you in sales.
So you are an individual contributor and now you are promoted to the sales leader
and you’re reporting to a highly technical founder that has never led sales before.
You now have the blind leading the blind and you better be ready
for a very interesting journey ahead
that’s going to challenge you in ways that you’ve never been challenged before.
And you’ve got to be resilient and you’ve got to be able
to see blind spots that you never anticipated seeing.
You’ve got to be able to fail fast and learn from that and adapt
and figure stuff out because your founder, they don’t know.
And you know what?
Just because you wanted the role and you hear some things
and you read some things, you don’t know because you haven’t done the role before.
So if you’re getting that promotion, it’s about exercising that muscle
of being uncomfortable with being uncomfortable and figuring it out.
And a lot of the time, that’s a really big bridge for people
to traverse.
Well, it’s kind of the Peter. Principle isn’t it sometimes, right?
Because you’re a good salesperson, right?
You’re probably one of the top salespeople if you’re getting promoted,
doesn’t mean you’re a great manager. Right?
And so I always kind of wonder anyway how sales organizations
deal with taking their best salesperson, moving them to a leader.
You’re kind of counting on them, adding some of their magic sauce
to the team, right?. Otherwise you wouldn’t do it.
Chip, it’s in the world that I live in, right?
So it’s a little bit different.
In Insightly, you’re a bigger company,
you have different layers, you have leaders of leaders.
And so you have
a function where you have career pathing and that person
is going to be set up for success in a much more significant way.
And the use case that I’m thinking of where it’s like OK,
these are early days and I hired a few salespeople
and I’m the founder and my top person is amazing
and I want to promote them because they say they’re ready for it.
And I don’t know what else to do with them and I’m afraid to lose them.
I strongly discourage that.
And the reason being is,. I get brought in a lot of the time
to clean up after a sales leader doesn’t work out.
And this is one of the main reasons why.
And it is that blind leading the blind a little bit and it’s not because
you didn’t want it to work out or the intention was bad.
In fact, the intention was really good.
It’s just you don’t know what you don’t know.
And it’s one thing to read something.
It’s one thing to go through a training.
So I think about this like content is the training
content versus context,
like how do you actually use it then versus competency.
And those three things are not mutually exclusive
just because you came up through the ranks to your point.
Makes sense.
And so anything else that comes to mind for the promoted up
through the ranks, new sales leader?
I mean in terms of pitfalls, Amy, yeah.
I mean, anything else that they need to watch out for?
Make sure that when you’re coming up through the ranks that you realize
if you’ve been an individual contributor or if you’ve been a front line manager
and you’re becoming a much larger executive,
the higher you go, the more visible
the role is and the more it’s not just about what you want to be doing.
It has a lot to do with your entire team.
So in leadership, when you get into it,
if it’s not about your people, you may want to rethink the role.
In addition to that, the higher you go so you’re a CMO,
Chip, your role is about marketing.
Guess what?
Your role is also about the entire business.
And if you can’t play nice with others in the sandbox,
you may not agree with your sales
counterpart all the time or your engineering counterpart
all the time or your accounting counterpart all the time.
But you all have to come together.
It’s like a perfect orchestration of things.
The CEO is the maestro, but the rest of you are all instruments
that come together that make the music sing right.
And if that doesn’t happen, that’s a real big problem.
And so I think when people get promoted, especially in sales, I see this thing
where it’s like sales against the world and it’s like, cut it out.
It’s an ecosystem.
You have to work well with everybody.
So this is
this is applicable advice, Chip, for when you’re coming up through the ranks,
but also when you’re coming into an organization as a leader as well.
It’s not just your agenda, it’s how it fits into the overall puzzle.
Makes perfect sense.
In graduate school, I had a professor that would say, the higher
you climb, the higher a monkey climbs, the more you see his butt.
And I think that’s true.
Yes, that is true.
When you’re a leader, you’re just exposed.
Right.. And you have to be very, very conscious.
It’s a different kind of role to move into from being an awesome sole contributor
where you really know your craft to moving into a leadership role
and trying to take that craft and teach it to others
and now become sort of a player in the organization.
That was a wise professor. Here for it.
Yeah. I thought so too.
It stuck with me, you know,
of the few things that have stuck with me from graduate school.
So you just paid it forward to me and I’m going to pay it forward to others.
I love it.
I mean,
who doesn’t want a little little monkey business analogy?
I need some monkey business.
So. OK, so Amy, let’s
pivot to the other scenario where there is
you’re hired in to a sales leadership role in a new business, right?
And so you have the business to learn maybe in the SaaS space,
the space we’re in, you have to learn the product
and you have to learn the customers and the problems you’re solving,
unless you came from specific
specifically within the industry and already know those things.
And then obviously you have to get to know
the individuals, you know, who are your strong performers
who are your weakest links, so to speak, and what do you really need to work on.
So where do you focus first?
Learning the business or focusing on your team?
I think you have to do a little bit of both at the same time.
So that’s where time management really comes into play. When you’re coming through
the doors, it’s all about listening.
So I want to listen to what’s happening with my team.
I want to listen to what’s happening inside of the business.
If I’m coming in as a sales leader, Chip,. I want to listen to what you’re doing
I want to listen to what operationally the business is doing.
So how do we think about when I have to go to procurement and if there’s a bunch of
security reviews and procurement takes
six months and it’s all this stuff like are we equipped for that?
What is our internal process?
How do we think about that today?
And then I’m making notes, right?
Because what I don’t love that happens when you’re coming through the door is
I’m just listening to do this to let people know, like I’m so happy to be here
and what keeps you up at night and how can I help you be a better seller?
And Chip, I’m here to work with you.. And all the while I’m just doing this,
and in the meantime, in the back of my mind, I’m like,
I got my own playbook and I’m just going to force it in here.
That is the worst thing that you could ever do.
Because here’s the thing about playbooks,
while you’ve learned a thing or two, mastered a thing or two
and probably messed up a lot more than a thing or two.
Yeah. Your playbook is merely a tool kit that’s a collection of things
that you have mastered and learned over time, but it’s not a one size fits all.
It’s kind of like when you’re building a house or remodeling a house
is a better analogy, which I just went through over more than 100 year old home.
You start getting into walls of things, the toolbox that you brought and
you get into a wall and you open up. Pandora’s box and you realize, Oh,
there is no insulation in this wall.
It was newspaper that fell down.
My tool kit no longer applies.
I got to bring in the insulation dude and his tools,
and that’s a completely different ball of wax
my point in making that analogy is
the only way that you really know what to do in your role
is to understand, just like in sales and the power of discovery.
And so I’m a big fan of you got to understand
your team, what you’re walking into, who’s doing what, who’s really strong
at what, right person, right role, right time.
And then you have to understand how it all correlates
to the larger ecosystem of, how do we do business internally?
Who do I go to for what?
And managing those relationships and strengthening them and building them.
Oh, and by the way, sales leaders, you better know,
like the back of your hand what your ICP is, that you’re able
to demo your product yourself, whether you’re not selling,
but you need to be able to help your sellers navigate.
And the only way that you can do that is if you can do the job yourself.
These are all things that you have to listen for
and learn and master coming through the door.
It makes sense.
So once,. I think through as a leader, say,
I get all those things right, right?
I come in,
I get to know my team kind of
at the same time,. I’m learning the business, I’m
learning the product,. I’m learning about the customers.
What are some of the markers
and checkpoints that I have to know if I’m doing a good job?
To know if I’m doing what I should be as a new leader?
So this is what I talk about a lot, where coming through the door
I want to set expectations early and often with my executive team.
So first and foremost, it’s going to be with my founder or my CEO.
What does good look like?
And let’s establish those milestones together for the first 30 days.
For the first 60 days, for the first 90 days.
And no, I’m not talking about
a 30, 60, 90 little tap dance that you do to get the job.
That’s not it at all.
I’m talking about mutually agreed upon expectations of, these are the milestones
of what I’m going to do.. The what you can actually expect from me
coming through the door and then when we sync up weekly,
biweekly, whatever our cadence is that that’s what we hold
as a sort of anchor together
and that’s what we talk about to make sure that we’re on the same page
because that’s the thing is people will say, we’ll talk in a quarter
and all of these other things didn’t happen.
And then it’s a big surprise.
And that’s a lot of what leads into the turnover rates that we see in
the industry is because you talk about it when it’s way too late,
as long as you’re talking about it early, some of the stuff can be course corrected
and the wrong assumptions don’t need to be made.
It’s when it’s like, get out of my lane,. I’ve got this, just let me do my thing,
I’ve got my playbook, I’ve got, those are big red flags for me.
All the time.
Where it’s like, just let me do my own thing.. I don’t need to tell you.
It’s like, well, actually, yeah, you do.
Because we’re working together and your decision affects all these other things.
It’s like a flywheel. So
That’s the biggest way to know is to figure out what does good look like together,
coming through.
This is also a really important trick
when it comes to interviewing.
Before an offer is extended,
these are the things to tether yourself to, to make sure that you’re aligned
so that on day one, it’s not this like big
scary thing of what is my onboarding plan?
It’s like, oh, we talked about this and it’s like a really comfortable shoe
that fits and you just walk the road together.
Makes great sense, Amy.
The road isn’t always easy to walk together, but you know what I mean.
For sure.
So any final thoughts?. There’s are some great stuff there.
The biggest final thought is, manage expectations early and often.
And I love the famous quote
If you fail to plan, you plan to fail.
Thanks so much, Amy.. We really appreciate you joining us.
You’re welcome. Thank you.
I appreciate it, Chip, this is lovely.
Of course.
And thanks to all of you for joining. Closing Time.
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