by Nicole Lee Comments (34)

Investment Banking to Sales at a Tech Start-Up: Do Deals and Make Bank Without Ever Staring at Excel Again?

Investment Banking to Sales at a Tech Startup

Can you use Excel to kill someone?


But it can definitely make you want to kill yourself.

If that’s you, the finance industry is probably not for you.

But you might still like working on deals in a fast-paced environment.

If you do, you have a lot in common with today’s interviewee: Nick Seaver, who moved from investment banking into an Account Executive role in the sales team at Clarizen, Inc.

Sales gets a bad reputation because people hear the word and immediately think of Glengarry Glen Ross, or pushy car salesmen.

But selling software to enterprise customers is a completely different ball game.

And it’s a great opportunity to get paid well, work in a team you like, and spend your time talking to people rather than staring at spreadsheets.

If you find a good enough role, you might even turn down multiple PE and HF offers to accept it – like our interviewee did:

How to Turn Down Multiple Private Equity and Hedge Fund Offers and Live to Tell the Tale

Q: Before we get started, can you give us a quick run-down of your background and the career changes you made?

A: Sure.

I went to a top school, entered banking when the economy was good to gain the skill set and exit opportunities, and then I worked in a few different groups in IB, such as financial sponsors, leveraged finance, real estate, and distressed debt.

But I grew bored with the financial modeling and technical aspects quickly, so I knew I wouldn’t stay in finance for the long-term.

At first, I tried to “fix” this by moving into a distressed debt group, but the novelty value wore off.

I also won a few PE offers, but I was tired of building models and writing documents after 4 years of doing it in banking.

So I pressed the “reset” button and went to business school instead. I figured it would give me time to think about what I really wanted to do, plus a lot of networking opportunities.

I realized that I wanted to work at a company that produces a real good or service, as opposed to a finance firm, which just provides capital or advisory services.

And I knew that tech start-ups are always looking for hungry, driven people, so I started looking for opportunities there.

I networked like crazy (over 60 informational interviews and meetings), and ended up joining the sales team at Skytree before moving to Clarizen (a cloud-based project management software company).

Q: OK, but if you wanted to work at a real company, why not move into a corporate finance career path or the strategy team?

Aren’t those more common for former bankers?

A: Yes, they are… but there are some downsides to those.

First off, at a normal company finance is more of a support function.

It’s not like IB/PE/HF where you’re on the front lines generating revenue with your skill set.

So not only are you still doing a lot of Excel work, but you’re more of a bean-counter than a deal-maker.

Strategy was somewhat interesting, but it relied more on analysis (and over-analysis…) and internal decisions, and I enjoyed talking to people and doing deals more.

Finally, relatively few people move from finance and strategy roles into CEO positions.

One of my long-term goals is to rise through the ranks and reach that level, and I felt that sales would be a better way to get there.

Q: Those are some great points – the fact that finance roles are “support functions” at normal companies often gets lost.

Before we get into the recruiting process, what do you actually do in “sales” at a tech company?

A: It’s mostly pitching, presenting, negotiating, and closing deals.

In a sense, it’s similar to what bankers do: you research potential clients, figure out their wants and needs, build the relationship, and then move in to close the deal when the time is right.

But we sell our software product rather than advisory services – and since I’m on the sales team, I’m not responsible for delivering or supporting the product, as bankers are.

Here are a few examples of what I do:

  • Lead Generation: I spend time finding new potential customers, including getting referrals from existing customers, researching companies, and cold-calling and cold-emailing to get to the right people.
  • Product Demos and Presentations: When a potential customer wants to learn more, I demo the product, answer questions, and try to move them across the “buy” line.
  • Contracts and Negotiations: When potential customers have questions on their contracts, I help negotiate the finer points and get deals done.
  • Work with Other Teams: I’ll have to go to other teams here to answer questions, figure out what customers want, and also give feedback to the product team on new features to consider.

Notice how there’s no “Excel” on that list.

I am still “on call,” but I’m not expected to be at the office 16 hours a day handling all the random problems that come up.

How to Hustle Your Way Into a Tech Start-Up

Q: So once you decided that you were interested in sales, how did you start networking?

A: First, I decided that big companies were a lost cause because I had an unconventional background.

Just like how it’s tough to break into bulge bracket banks if you’re a career changer, it’s also surprisingly difficult to break into large tech firms, at least if you want to do sales and you already have full-time experience elsewhere.

They looked at me and said, “We want someone with sales experience – why would an ex-banker with an MBA from a top school want to join our team?”

At small tech firms, by contrast, they care more about whether you can deliver results.

Compensation in sales roles is heavily tied to results, so they’re not going to lose a fortune if you don’t perform well.

Q: So once you decided to focus on smaller firms, what was the next step?

A: I relied heavily on LinkedIn, and I started by making a list of all the tech companies in my area that fit that the profile.

But there’s a small army of them in the SF area, so I had to be more specific and focus on software companies (since it’s one of the higher-margin businesses in tech).

So I narrowed down my list, started searching for the companies on LinkedIn, and reached out to anyone who was connected to employees at those companies.

Each time I met with or spoke to someone, I would ask for 3 more introductions at the end; I ended up conducting around 60 meetings total.

I won the offer like this:

  • I contacted a venture capitalist who introduced me to a well-known salesperson in the Bay Area.
  • Then the salesperson introduced me to an equity research analyst who covered tech companies.
  • Then the research analyst spoke to a recruiter on my behalf.
  • And then the recruiter introduced me to a frat brother of his who was working at a start-up that was hiring at the time.

Q: OK, but couldn’t you have contacted the recruiter directly and saved a lot of time?

A: No, and here’s why:

PE firms and hedge funds rely on headhunters to fill a huge percentage of their roles at all levels.

But in the tech industry, recruiters mostly care about engineers, and small firms don’t even like to use recruiters because of the placement fees they charge.

So if you’re going for non-engineering roles and you’re focused on true start-ups (i.e. not companies with hundreds of employees and $10+ billion valuations), you probably won’t have much success going through recruiters.

Q: Thanks for explaining all that.

What types of questions did you get when you finally made it to interviews?

A: Typical questions were:

  • How can you immediately add value to our company?
  • What are you going to do your first day to generate sales?
  • Describe your strategies for finding potential customers and closing deals.

Here’s what the process looked like:

  • First Round Phone Interview: I spoke with the VP of Sales.
  • Second Round In-Person Interview: I spoke with the VP of Sales and Director of Sales.
  • Final Round In-Person Interview: I spoke with the CEO and CTO.

The focus of each interview was different – people at the VP level and below (“managers”) spent more time understanding why you want to do the job, if you can tolerate some monotony in the beginning, and if you’re motivated to excel.

The first few months of any sales job can be monotonous as you “learn the ropes,” such as how to cold-call or handle inbound leads; it will also take several months to really understand the product you’re selling.

C-level executives such as the CEO and CTO focused more on assessing my “fit” with the culture of the company and whether or not I bought into their vision for it.

You really need to do your homework on the company, its competitors, and the industry as a whole to answer these questions – it’s not like IB interviews where the questions asked are similar, even at different banks.

For sales roles, you should not be shy about what you’d personally gain from the role – money and promotions – because they want people who are driven to succeed.

Q: Thanks for sharing all that.

Beyond doing the research, how do YOU figure out if it’s actually a good company to join?

A: It can be very difficult because tech start-ups are all over the board and it’s up to you to ask good questions to the right people.

What matters most is how much you learn, and that will depend largely on the people around you.

I would be very careful to understand the composition of the team and your fit with the manager – if the team or your manager is weak, it will be a challenging experience.

Q: OK, but what specifically can you ask to determine any of that?

A: I spent a lot of time researching the investors in the company, the pedigree of the management team, and my manager’s background.

You can find a lot of this on resources like CrunchBase and LinkedIn; I focused on companies with significant funding (> $50 million) and more than 100 employees because I wanted firms with good market traction.

Once I had done that research, in interviews I asked questions such as:

  • How many customers do you have?
  • How quickly is your customer base growing?
  • How many people do you have in various functions?
  • How many people are you looking to hire?

You want to assess how much revenue they’re generating, how quickly they’re growing, and how profitable they are.

Unfortunately, private companies will rarely, if ever, answer these questions because the information is closely held by the management team and the Board.

If you have a connection to a Board member you can sometimes use that to get this information, but even Board members can be biased because they’re also recruiting talent (i.e., you!).

So the best method is to assess the quality of investors, the management team, and your manager.

A Day in the Life of a Sales Rep: Coffee is for Closers?

Q: So what is an average day in your life like?

And how much time do you spend doing “hands-on” work vs. managing other people?

A:I get in at 7:45 AM each day, and I spend the morning on customer calls.

After that, I follow up with anyone who has expressed interest in our products.

Usually, this consists of calling them to see why they’re interested, what their objections are (objections = the first sign of serious interest), and if they want to get a free demo.

On some days I’ll already have meetings set up, so I’ll head over to the company, present to a team there, and give them an overview of our product.

Since we sell enterprise software, the sales cycle is very long and it takes many meetings to get all the decision-makers past the “purchase” line.

If it’s an earlier stage meeting, the focus will be on the product demo and the features/benefits; later stage meetings are more about negotiating the specifics of deals, the legal points, and finalizing the pricing.

Also in the afternoon, I may give customer feedback to the product marketing team, speak with anyone that needs to be in the loop, and even interview candidates who want to join our team.

I leave at 6 PM, so the average day is around 10 hours.

There’s some travel involved, but much of it is local and I tend to do most sales work via the phone, especially in earlier-stage deals.

Q: What about the culture and hierarchy?

A: I report to the VP of Sales directly. The VP of Sales, in turn, reports to the CEO directly.

Depending on the size of the company, here is the general hierarchy:

  • CEO
  • VP of Sales
  • Director of Sales – Front-line manager (exists at larger companies)
  • Account Executive – Manages the sales process and relationships with customers

In some ways, the culture is similar to banking because sales also attracts smart, intense people who want to win and who will work hard to get there.

And just like in banking, you’re watched very carefully and every decision you make can be questioned.

Sales reps also have quarterly quotas to hit, which adds to the pressure.

On the other hand, no one here expects you to be in the office for 16 hours a day.

Even if it’s a start-up, there’s no point in being here at 2 AM because customers won’t even be around.

Another cultural difference is that there’s more respect for people regardless of the level they’re at.

No one here ever thinks, “Well, we pay you a huge amount of money so we can treat you like an animal and make you do whatever we want, 24/7.”

Q: Speaking of getting paid a lot, what is the compensation like?

A: Cash compensation is lower than what you’d earn in IB, but you also get equity here, so the potential upside is quite high if the company does well and goes public or get sold in the future.

Account Executives get paid based on the size of the customers they cover and the size of deals they close; compensation is generally split 50 / 50 between cash and commissions.

The total compensation for an Account Executive that hits his/her numbers is known as “On-Target Earnings” or “OTE.”

A big advantage of sales is that when you go over quota, you get massive accelerators which can significantly increase your compensation.

The best sales reps at start-ups actually make more than the CEO!

Another difference compared to banking is that commissions are paid on a monthly or quarterly basis, and paying them out like that is a legal obligation of the company.

Q: That’s all very helpful, but can we get some specific numbers on the comp.?

A: Sure, here you go (all figures in USD):

  • Account Execs covering Small and Medium-Size Businesses: $100-$120K OTE, on the low end.
  • Account Execs covering Enterprise: $250-$280K OTE.
  • Outperforming Sales Reps: $750K up to potentially $1 million in good years.

You also get equity, but the exact percentage depends heavily on your bargaining position; experienced sales executives have more power than career changers.

I would take a look at Andy Rachleff’s “Startup Salary & Equity Compensation” tool to get an idea of 25th-75th percentile salaries and equity grants.

You’ll see there is a massive variance in the compensation for sales reps, because so much depends on your performance and experience going into it.

Even though sales can be very lucrative, you should not think about the compensation or the discount to IB/PE pay that much – make your decision based on the type of work you’ll be doing and the team you’ll be joining.

Especially if you’re coming in after several years in finance, you’ve probably saved more than enough money to be comfortable…

Future Plans: Sales to CEO?

Q: What are your future plans? What options do sales professionals typically have?

A: My future plan is to start a business or rise up through an organization and become the CEO. I like this role quite a bit, and I definitely fit in more with a normal company than I ever did in finance.

There are plenty options for sales professionals: they can move to product management, marketing, or most other divisions at the company.

Q: Based on everything we discussed so far, who would fit in best with the sales team at a tech company, and why?

And who should avoid it altogether?

A: Let’s start with who should avoid sales: If you’re introverted and prefer to work on your own rather than talking to people, sales isn’t for you.

If you like to analyze and analyze and analyze rather than taking quick action, sales is also not for you.

People who should pursue sales: If you are a former athlete and you enjoy high-pressure environments, you may love it.

If you’re not afraid of rejections and you don’t care about repeating the same thing over and over again until you perfect the craft, you would also love sales.

Many people from top universities “look down on” sales roles, but in my opinion it’s far more interesting than spending your time staring at spreadsheets and documents.

It’s also a great way to get to know people in other industries, since your customers will come from all walks of life.

Q: Thanks a lot for your time!

A: My pleasure.


About the Author

Nicole Lee has been serving as an Executive Career & Networking Coach for senior professionals in investment banking, asset management, private equity, and global Fortune 500 companies since 2012.

She has helped 500+ candidates land finance roles at firms such as Morgan Stanley, Macquarie Capital, and UBS.

You can connect with her here.

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Read below or Add a comment

  1. Hi Brian,
    I am currently a credit analyst at a community bank and only making 40k, talk about being underpaid… I want to make more money, a lot more actually. At least paid for what I’m worth. I am a former college and semi pro athlete was captain of my teams so I know all about leadership. I can’t stare at spreadsheets all day, I’m more of a people person. I’ve worked in public accounting and automotive both internships and have been at the bank for a little over a year now. I’m basically living in poverty and counting every penny I make. I was considering making the move over to sales (wholesale mortgage lending). Just wanted to see what your thoughts were on this?

    1. It might be a good move, but you won’t necessarily start making a ton of additional money right away because you need time to ramp up in sales. But if you’re good, yes, you could earn a lot more.

  2. Hey there,

    GREAT article, loved it. Quick question from someone thinking about changing from banking to fin tech sales. What preparation can you recommend (e.g. Best books for sales pitches, articles on effective communication etc)? Are there any great resources out there you could recommend? Can very well be quite broad, from how to train your voice effectively over the phone to negotiation skills. Would highly appreciate a reference starter kit to prepare for this new role.
    Thank you so much for your help.

  3. Great article – I am in the middle of the transition myself and had many questions. I’ve found one needs to sit back and really think about their transferable skills and how to pitch their background. Tough transition but once you’re in the game you’re in it for good. Would love to see the cover letter he put together explaining this transition.

    1. Thanks! I’m not sure if he used an official cover letter, as the transition was far more about networking than official applications.

  4. Hi Nick,

    I’m a junior who is pursuing an undergraduate degree with finance and business analytics concentrations at a target business school.

    My primary target is sales roles and I’m very happy that Brian posted this interview with you.

    Please let me know if you can put me in touch with anyone who can interview me for roles in enterprise software sales, start up sales, or other related fields. I’d also be interested in sales roles at Clarizen.


    1. Hi SR! Glad to see you are champing at the bit to get into sales! I recommend waiting until your senior spring to start looking. Sales managers at growth companies hire on a “I-needed-you-yesterday” basis. You might be able to snag a sales role at a larger company a year in advance; however, I am not as familiar with their recruiting processes.


      1. Avatar
        M&I - Nicole

        Nick, you’re awesome. Thanks for commenting and helping our readers!

  5. Hi M&I/Nick,

    Long time reader/BIWS purchaser. Have to say, this is one of the most influential articles I’ve read on the site since I’ve been reading (5+ years). I felt the same way as Nick, though do not have nearly the credentials. I’ve just accepted a sales position at a late stage private company ($50M+ funding, almost 200 employees) in the South Bay coming from Finance in San Francisco.

    One thing I will say – I do not necessarily agree with Nick’s statement regarding recruiters. While they do typically focus on the technical engineering jobs, there are many recruiters here in the Bay Area that focus on sales. I honestly wouldn’t have the job offer I just received had it not been for a recruiter. It’s especially troublesome coming from finance because every interviewer I had started with “Why would you leave finance for sales?” The boutique software sales recruiters all come from big companies such as Oracle, SAP, etc. and have a vast network that you just could not tap coming from finance. Look at the sales executives of start-ups, most, if not all, are coming from one of the big legacy software companies.

    Anyways, thanks again for the write-up. I can’t tell you how helpful it was for me when transitioning from finance to sales.

    1. Avatar
      M&I - Nicole

      Cameron, thank you for your comment and for sharing with us your experiences. I am glad you find the article useful!

    2. Cameron, I enjoyed reading your comment! Glad to see there are other folks who are independently following a similar path. I generally agree with your point on recruiters. I actually found my software sales job through a great recruiter in the East Bay.

      You seemed to have a similar experience as me in recruiting. I was trying to convey the view that recruiters are not actively seeking “financy” people for sales roles. I had to “sell” myself to the recruiter to get access to his opportunities. Recruiters and HR gatekeepers are generally wary of folks who switch careers so the burden of proof is high.

      Best of luck on your future gig! To many quarters of out-performance!


  6. This is a great article! It’s great to see the non-obvious paths and career options, in additional to the usual high finance stuff.

    Is there a way to “test the waters” with sales, without leaving one’s current field and hoping for the best? If things don’t work out, I can’t imagine that it’s easy to get back into sales after a dismissal.

    Thanks for your insight!

    1. Avatar
      M&I - Nicole

      What you can do is take a commissions only part-time sales role. But I think this will require a bit of research

  7. Avatar

    I worked in enterprise sales at a large tech company (Salesforce/Oracle/Microsoft) for the past 2 years and this is a great interview.

    I learned that being an account executive is definitely NOT for me. I’m too introverted and enjoy analysis – I’ll be getting an MBA to get out of sales and into strategy.

    That said, I learned a ton and sales skills trade at a massive discount in the classroom – invest in them early and reap the rewards.

    1. Thanks for adding that, always good to have the experience even if you end up going in a different direction.

      1. Avatar

        My pleasure.

        Most people don’t realize just how important sales is. When you’re interviewing for a job, you’re trying to sell the hiring manager on your capabilities.When you want to go to Vegas for your buddies bachelor party, you’re trying to sell your girlfriend that it’s actually a good idea :).

        Even in highly technical fields salesmanship is of the utmost importance – Larry Ellison and Bill Gates were both solid programmers, but their ability to sell the vision of the relational database and a “PC on every desktop” respectively is the reason they are billionaires and titans of technology.

  8. Sure, please do. I look forward to your email soon.

  9. Hi Brian,

    I am an example of someone who went to from a BB IBD to a successful tech startup that I helped built from the ground up. I would love to do an interview or at the least offer you some insight that you could use for future articles. Please send me an email and I’d be more than happy to provide add some value.

    1. Thanks! We will contact you soon.

  10. Hi I’m an undergraduate student at a top tier state school (think Michigan, UVA, Berkeley), I was recently admitted into my university’s business school and was also accepted into the School of Foreign Service at Georgetown. I was wondering if you would recommend staying at my current school or transferring to Georgetown? SFS is an incredibly prestigious program and would offer me more flexibility if I decide later in life to go into international affairs or get an IR graduate degree. However, I think that my current school places stronger for business. I was wondering if you thought that a) going to SFS (and majoring in international econ) would reduce my potential for getting a BB offer as compared to my current school, and if b) transferring schools is looked down upon by employers?

    1. Transferring schools is not looked down upon. I don’t think this choice makes a huge difference for getting into IB, if your current school has solid recruiting it is probably about the same either way. So you should decide based on what you’re personally more interested in.

    2. Avatar
      M&I - Nicole

      I’d recommend transferring to SFS; G’town has very strong alum connections on Wall Street and you can also do IR/int’l affairs, etc if you choose down the line. No, transferring is not looked down upon by employers as long as you can justify why you transferred, and no transferring to G’town isn’t likely to reduce your chances of breaking into banking, *unless* you can’t deal with the workload and get a GPA less than 3.5

  11. Avatar

    Great comments – appreciate it.
    Is it possible to move from Sales Ops to sales (account executive), business ops or corp dev as your career progresses?
    I recently was offered a position as a Sales Ops/Strategy analyst at a top tech firm but am wondering how a career in this role would progress. Is it a bad idea to start in such a role? I just graduated.
    I’m interested in how much account execs make as I always though product managers earned the most in a ‘non-technical’ role at tech firms.

    1. Yes, I think it’s possible and it wouldn’t be a bad role to start out in. You can probably move to the sales side, but you should do so sooner rather than later or it will just get harder and harder to make the move. I don’t think product managers make much compared to the top sales reps because they are not direct revenue-generating functions.

    2. Avatar
      M&I - Nicole

      Lseactuary – while we understand you support our site, there’s no need to change user name, and please respect our comments policy, as I’ve mentioned before. Please refer to my previous comment on, in response to our policy and the numerous questions you raised.

      To clarify how this site works: we attempt to answer comments and questions free of charge, when possible, in the interest of serving this community. You have asked a significant number of lengthy questions, and it costs us staff time to respond to your questions – as a result, there is a limit on what we can answer for free in response to these types of in-depth questions.

    3. “Is it possible to move from Sales Ops to sales (account executive), business ops or corp dev as your career progresses?”

      it’s certainly possible to move to sales or business ops, but not corp dev. at software companies, the corp dev function (which typically only exists at larger, more established companies as opposed to startups) is typically staffed by ex-bankers and consultants.

  12. Great article. I work in corporate development team in one of the technology companies in India. Although it sounds good, this role really is the support function. Account executives in Sales make much more money (almost 50% variable though) than executives in Corporate development. Also if you are selling enterprise product, you will get into much more varied deals than vanilla acquisitions e.g. normal M&As, licensing and reselling agreements, co-development agreements etc.

    1. Thanks for adding that! Yes, sales seems to have a lot of advantages over corporate development.

  13. Sales Ops / Strategy is typically more of an analytical / operational function. People in this role generally do not have customer contact. These folks do things like analyzing compensation plans or figuring out the optimal territories.

    It is a little bit confusing because sales people sometimes have non-standard titles. For example, start-ups have lately been changing the names of sales people from account executive to “Teammate” or “Enterprise Advocate.” The key to understanding whether or not someone is in “Sales” is to see how they are compensated, ie are they carrying a quota.

    1. Thanks for adding that!

  14. Avatar

    Great article and very insightful (covered questions/concerns I had about banking too!)

    Just wondering if ‘sales’ at a tech company means ‘sales ops/strategy’ or is the sales team called ‘sales’? I’ve seen account exec roles in tech companies but this is different from sales ops/strategy so I’m a bit confused by this.

    1. Thanks! Yeah it varies by the company – it can be called either one and depends a bit on the stage and size of the company. Sales ops/strategy would probably be a bit less hands-on with customers (though anyone with more knowledge feel free to correct this).

    2. Sales ops is different than sales.

      Source: Personal experience.

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