PODCAST 01: Walking the Road from Individual Contributor to Management

In this inaugural episode of the Sales Hacker podcast, we talk with Kiva Kolstein, Chief Revenue Officer at AlphaSense.

In Today’s Episode:

  • How to map your career from individual contributor to manager
  • Why you should spend time with and invest in your new hires
  • How to know if a company is a good fit for you and your skills
  • How a cohesive leadership team should function

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Show Agenda and Timestamps

1) Show introduction [00:12]

2) About Kiva and AlphaSense [1:36]

3) Kiva’s sales story [3:02]

4) Going up the sales career ladder [9:00]

5) Balancing patience and ambition [16:00]

6) Picking the right company [18:30]

7) Kiva’s playbook and the importance of choreography [29:00]

8) How to interview properly [30:00]

9) Territory planning and territory creation [33:30]

10) Quick-fire questions [39:35]

11) Sam’s corner [44:11]

If you’re more of a reader, you’ll find the full transcript below.

Sales Hacker Podcast—Sponsored by Node

Sam Jacobs: Hi everyone and welcome to the Sales Hacker podcast! I’m your host Sam Jacobs, founder of The New York Revenue Collective.

Before we start, a quick thank you to this month’s Sales Hacker podcast sponsor Node. Node’s AI discovery platform can understand the meaning, context, and connection between any person or company by proactively surfacing opportunities that are highly relevant and personalized in real time.

Node is creating an entirely new paradigm for sales and marketing professions to grow pipeline and accelerate revenue philosophy. 

Now on with the show.

This is Sam Jacobs. I’m the founder of the New York Revenue Collective. I’ve been building businesses in New York City for the past 15 years and this is episode one. Thank you so much for joining us for episode one. We’re excited and honored to have Kiva Kolstein, a Chief Revenue Officer of AlphaSense and somebody that’s been a friend of mine for a number of years. Welcome, Kiva.

Kiva Kolstein: Thanks Sam, great to be here.

Sam Jacobs: Well, we’re excited to have you. You’re one of the most respected and recognized revenue leaders in New York City and AlphaSense is one of the fastest growing businesses. What we want to do over the course of the next period of time is really chat with you about where you’re from, your origins, what got you into sales, and then we can dive deep into some topics as they emerge. Does that sound like a good idea?

Kiva Kolstein: Sounds perfect.

About Kiva Kolstein and AlphaSense: Baseball Card Stats

Sam Jacobs: Awesome, so we’re here with Kiva Kolstein and we want to do the quick baseball card stats. Kiva, what’s your title?

Kiva Kolstein: Chief Revenue Officer.

Sam Jacobs: What’s the company that you work for?

Kiva Kolstein: AlphaSense.

Sam Jacobs: Now give us a rough annual recurring revenue range for AlphaSense.

Kiva Kolstein: We are in the $15 to $20 million range.

Sam Jacobs: How many folks are on the team? What’s the size of the team that you’re responsible for and walk us through how it’s organized?

Kiva Kolstein: We have about 40 people on my team and my team consists of customer success, which includes account management and product specialists and sales. The sales team is set up in two teams, we’ve got a team that’s responsible for selling into the buy side and sell side, and a team responsible for selling into big corporations. Each of those teams has a VP of Sales. Then supporting both of those teams is an SDR layer. In addition, we have sales ops and sales enablement.

Sam Jacobs: Wow, and tell us about your growth plans for 2018.

Kiva Kolstein: Our goal is to double revenues in 2018. In terms of the number of people, we’re likely to grow the sales org by about 50% this year.

Back to the Very Beginning: Kiva in Sales

Sam Jacobs: How’d you get into sales and how did we end up on a Zoom call across the Atlantic Ocean together on a Tuesday morning?

Kiva Kolstein: Great, happy to do that. The coolest part of my story actually begins long before I even thought about sales, long before I really thought about anything. My parents decided to, on a whim, quit their jobs, sell their house, sell all their possessions when I was three years old and take me on an 18 month trip around the country.

We spent 18 months living in a trailer visiting every state and Mexico. Over that period of time obviously we spent a lot of time together as a family, but my father wrote a book called Everybody Should Quit at Least Once. I didn’t know anything about the book that he was writing, nor did I know anything about the trip that I was on. I was only three years old.

Sam Jacobs: Where did you guys start from?

Kiva Kolstein: We started from Maplewood, New Jersey.

Sam Jacobs: Wow.

Kiva Kolstein: We landed in Rockland County, New York. That’s where the trip ended and we settled down.

Sam Jacobs: How’d that transform the rest of your life?

Kiva Kolstein: Well I think a couple things. One is the importance of doing what you love and making sure that you’re always sort of checking yourself to remember that you only live once and you should spend every minute of every day doing the things that you love.

Individual contributor at Winstar Communications

Sam Jacobs: Tell me more about that foundation, so how did it lead to a career in sales or the animus was really doing things that you love, and how did you figure out even that you loved sales? Because I think your original background was in political science if I’m not mistaken.

Kiva Kolstein: Yes, right, exactly. With a backdrop of doing what you love, that’s what I set out to do after college. After I graduated with a degree in political science, I decided I wanted to go to law school, my parents suggested I take a year off between graduation and starting law school and get a job and see what it’s like in the real world.

I went to work for a company called Winstar Communications, which was a small local telecommunications company in the midst of the telecom deregulation of 1996.

It was an awesome time, a great time to be working in the space. I sold to big Fortune 500 customers, I crushed my numbers, I won national and international sales contests across 500 or 1,000 person sales organizations. I literally had trucks backing up to my apartment with prizes won from these sales contests.

Sales management at Global Crossing

Sam Jacobs: Let’s keep going through your background. So Winstar Communications is the beginning.

What happened next?

Kiva Kolstein: I stayed another year after having done well my first year and moved on to a company called Global Crossing.

It was actually an interesting time to be at Global Crossing. Global Crossing had just bought Frontier Communications.

Much smaller in terms of the number of people and revenue generated company buying a much larger one. I think at the time I was with Global Crossing, we had something in the neighborhood of 500 or 1,000 people and we bought Frontier Communications, which had maybe 10,000 employees.

I began as a manager at Global Crossing. I stayed on there a couple of years taking on two or three different teams as a general manager in New York and had a bunch of success there.

Building Your Sales Career Ladder

Sam Jacobs: The Sales Hacker audience has a lot of SDRs and a lot of entry level account executives, thinking about mapping a career that eventually ends up in management.

Do you have any tips, tactics, insights there? Because you’re both an example of this distinction going from an individual contributor to a manager, how do you think about guiding people that are trying to figure out what’s best for them?

1) Hit your numbers

Kiva Kolstein: I think the first thing is to hit your numbers. No matter what you do, no matter where you ultimately want to go, it all starts with you mastering your craft.

As an individual contributor really learning how to choreograph the entire sales process, learning how to break down your sales cycle into its smallest components and master each of the phases. It begins with a phone call or an email and you move into that first meeting, the sales deck, the demo, the discovery call, objection handling, negotiation, closing, etc.

2) Be selfless: behind the scenes vs. at the front-lines

That’s the first most important thing you can do. Beyond that, the best sales managers are selfless! The big difference between individual contributorship and management, from my perspective, is frontlines versus behind the scenes.

You’re standing on a stage in front of the audience as an individual contributor and you are behind the scenes as the producer or the director pulling the strings as a manager. You have to be selfless and interested in elevating the folks who work on your team and giving them the glory. At your fingertips, you need a repository of best practices that can be shared across a team.

3) Work as ONE team

I often hear from management candidates that they think of themselves as entrepreneurs and they have an entrepreneur mindset. That’s a good thing on the one hand, because you do need to be crafty, gritty, and willing to roll up your sleeves and pivot on the go.

But on the other hand, entrepreneurs, many times begin by working alone and that is the opposite of what I see in good management. You really need to understand how to quarterback a sales process or pull from different parts of the organization for your sellers. Whether it’s engineering or product help or even the finance team or marketing team.

The Road to Being a CRO

Sam Jacobs: For a lot of folks that are listening, probably their career destination and their career goals are to at some point be a CRO.

What work do you think over the last, maybe 10 years, have been the important inflection points that led you to where you are today?

Kiva Kolstein: I was in management through CPI at a company called Castle. I actually took a step back in terms of responsibility by joining Gerson Lehrman Group, GLG, where I met you Sam and decided to help found the corporate markets division for this company.

1) Ask for a seat at the table

I began, as an individual contributor again there. I think that was really a turning point in my career because it was a startup within a bigger company. We had a bit of a safety net in that if it didn’t work out, there was a bigger company to support us.

I was involved in every facet of building this business, even as an individual contributor. A seat at the table. Thinking about pricing strategy and customer segmentation and territories as we realized there was an appetite for access to experts.

We began to build a business there. Regardless of my title, my responsibility expanded far beyond selling to customers. I was thinking about the handoff between sales and service, what is now called account based selling or ABS. But really thinking about how we could expand into all of these big Fortune 500 customers that we’d begun to sell to. When do we bring on an SDR team?

2) Punch above your weight

Even back then, as an individual contributor for this startup within this larger enterprise, I was getting involved in things that would be more like the head of sales or CRO. That was the big turning point. We built a 50- or 60-person company there. We grew revenues in GLG to $30 or $40 million over the six or seven years that I was there.

Balancing Patience and Ambition

Sam Jacobs: Do you have a framework for what guided you to take what you consider to be a slight step back in terms of title to GLG or maybe some advice for people that are balancing those two paths right now in their career?

Kiva Kolstein: It’s a great question. I think one of the most difficult things to do as you’re building your career, not just in sales but just in general, is balancing patience and ambition.

Hard for me, hard for everyone, and so I don’t know that there’s a recipe for balancing patience and ambition.

Focus on the opportunity at hand

It’s mostly about the opportunity. So when I talked to SDRs who aspire to be AEs or AEs who aspire to be managers, what I want to sell them on, what I want to talk to them about is the opportunity that exists at this company for them and try to show them not just a path to whatever comes next but a path to the job after that or the job even after that.

Train your new hires to smash their next job

I think too often sales managers bring on new hires and teach them the job that’s right in front of them. Perhaps even some of the better ones help them close deals and achieve their target. Are they delivering general management skills to help this seller manage a PNL? That’s the kind of additional support that I think folks need today or really need to believe they’re going to get from you before they join your company.

How to Pick the Right Company

Sam Jacobs: I think that’s great advice!

Specifically for the listeners out there that aren’t familiar with AlphaSense, tell us about that company and tell us about the factors that led you to take the role as Chief Revenue Officer at AlphaSense.

What’s paramount is the opportunity

Kiva Kolstein: Sure, there are five or six things that needed to be true to get really excited about AlphaSense and the role. Most importantly, as I just mentioned, the opportunity. What about this company makes it an exciting place to be regardless of your title or your role?

Understand how big the market is

It’s a gigantic market! It’s a market that already exists that does not need to be manufactured. All of the knowledge professionals who work for these different companies. So if you’re on the buy side it’s an analyst, a PM, an MD, a director of research, a CIO. If you’re inside of a big corporation it’s M&A, strategy, competitive intelligence, investor relations, BD, corp comms.

Clearly define what “market” means

Sam JacobsWhen you think about big market do you just think about the number of people, the average amount that they spend, the total amount that they spend, how do you think about it?

Kiva Kolstein: Great question and all three.

AlphaSense is a SaaS product and we sell licenses to individual users inside these companies. We think about the number of users within a company that might potentially buy, how much they’ll spend, and then by the market, the total revenue opportunity that we may be able to realize by selling into these set of customers. (Read: BANT and Beyond: Advanced Sales Qualification for SDRs & AEs)

Are they trying to access a budget that doesn’t exist?

Sam Jacobs: Another common fallacy that I’ve seen is everybody assumes their product is going to access newly created budget.

That the decision maker or the economic buyer is going to create new money for their solution. Are you guys taking existing budget from other spends or are you in one of those rarefied situations where they are actually going out and getting more money and new money for your solution?

Kiva Kolstein: At AlphaSense the budget is already there. It’s highly likely that if you’re a knowledge professional in one of these companies you are spending money on Bloomberg, or Thomson Reuters, or CapIQ, or FactSet, companies like that. If we can differentiate AlphaSense and show you how you can gain access to the very same content more quickly and you can find what you’re otherwise missing, we can shift budget from one of those companies or other companies like them to AlphaSense.

How many sales until you cross the finish line?

How many sales do you need to make in order to get your deal done? If you first have to convince them that access to this kind of content is important, or access to an expert who might help you think about moving your business into a new market is important, well that’s sale number one.

Then you’ve got to convince them, sale number two, that doing it through your firm is a good idea. With AlphaSense sale number one has already been made, and so, you’re speeding up the sales cycle.

Does the product already serve the needs of the market?

Sam JacobsWhat are the other factors when you’re evaluating and picking a company besides the product and the market that you’re considering?

Kiva Kolstein: Well, the first is definitely the size of the market. The second is the product and you’re right we’ve got a product. But I think I’d spend a little bit more time on that one because I’ve been part of or I’ve advised companies where the go to market strategy is far out ahead of the product.

What was really important is joining a company whose product already serves the needs of the market. That it’s not some future road-mapped product but the product as it exists today supports the needs of the market. Of course, it will continue to evolve and get better over time, but what I didn’t want is sellers having to sell six or 12 months into a roadmap.

Do they know when to re-prioritize and make a customer-commit?

Sam Jacobs: You see companies raising $10, $15, $20 million around a B or a C round. The assumption being that they figured it out and now is the time to scale. But in actuality what’s happening is exactly what you just described. Sellers selling into a roadmap that is sometimes six to nine months out ahead.

Kiva Kolstein: Yes I think it’s an epidemic. I really do.

You’re putting pressure on the sales organization to go out and sell these deals, when in fact in order to do that you’ve got to sell so far into the roadmap that you’re just not going to have happy customers. This leads to churn and there are all sorts of problems that come as a result.

Kiva’s Sales Playbook and the Importance of Choreography

Sam Jacobs: Let’s move into a few tactics because you’ve learned a lot of lessons from your time at startups, and I think it’d be helpful to share some of your key lessons and some of the elements in the Kiva Kolstein playbook that you rely on, that you think are particularly successful. Walk us through some of your frameworks.

Kiva Kolstein: Choreography is sort of the overarching framework. Sam you and I have talked a lot about that, and I care deeply about sort of choreographing the entire process for sellers, for managers, for ops, for really everyone in my organization—sales and service.

How to make sales hires the right way

Sam Jacobs: I think a lot of people would nod their heads. The next question is—I don’t know how to hire somebody properly. I don’t know how to hire somebody effectively. What’s your framework for making that decision the right way?

1) Involve a lot of people in the hiring process

Kiva Kolstein: I think getting lots of people involved in the hiring process is a good first place to start. Making sure that everyone who is interviewing a candidate is looking for something unique.

It will give the candidate a better experience not to have five or six of the same interviews. We’ll focus questions in a way that can deliver to me—who may be the hiring manager—insights around each one of these characteristics that I may be looking for.

2) Chase the candidate’s story

Sam Jacobs: What’s your favorite interview question? Give us something we can take with us.

Kiva Kolstein: I think it’s less about a favorite interview question. It’s more about the story I want to hear from a candidate. It’s important to go all the way back to the beginning. I told the story at the outset of this conversation about my parents and the trip around the country and how that, to some extent, has stayed with me and built a foundation as I think about what I do with my day.

I want to hear about elementary school and challenges that they may have faced or had to overcome. Whether they’ve played sports in high school or played an instrument, why or why not. About why they chose the college they did.

Territory Planning and Territory Creation

Sam Jacobs: Kiva, what else do you think is important? You’ve talked about hiring a little bit, but give us a little bit more of your framework for helping build and scale a startup.

Kiva Kolstein: Coming up with a territory creation plan you can convince the existing sales team that there’s enough TAM, total addressable market, inside of their prospect universe to give them the opportunity to double or triple their target is a really important part of managing a team. At the same time, when you are scaling be able to deliver to new hires the same opportunity, the territory that gives them the opportunity to double or triple their target.

Sam Jacobs: In some sense, you’re not even just talking about territory creation but around the entire investment that you need to make for a new seller to make them successful, which might also include SDR support or marketing support or some commitment around how you’re going to help them build that pipeline within the territory.

Look beyond geographies

Kiva Kolstein: Absolutely that’s true, and then I would say those are additional peripheral learnings around territory creation.

One of the most difficult tasks is literally creating territory, and so how do you do that? Well, you’ve got to get creative and go beyond geography. We’ve through about verticals, we’ve thought about sort of ABS, so when you’re starting the company or early days you’ve got sellers who got 200 or 500 or 1,000 companies in their territory, and as you bring on more sellers you’re shrinking that territory.

Focus on specific accounts and deal sizes

ABS is this new term but an old strategy. It’s focusing in on very specific accounts and understanding the customer personas that we’re selling into getting into these accounts. Then comes, determining how much revenue you can generate with one account over the course of the next year and then build a marketing and sales plan around getting that revenue.

When you do that and you do that effectively, you can now convince a seller that instead of needing 200 or 500 accounts in their territory, they may only need five or 10. That’s a really important part of scaling a sales org is getting to a place where a seller only believes they need five or 10 accounts in their territory to achieve their target.

Manage the SDR-AE handoff carefully

Sam Jacobs: At AlphaSense, if I’m a seller, am I just focused on new business or do I get to keep the account after the sale so I can push for expansion and upsell?

Kiva Kolstein: On the buy-sell side, you immediately hand that account off to an account manager. Mostly because additional analysts buying access to AlphaSense inside of a hedge fund doesn’t require a lot of additional selling. On the corporate side you keep the account as an AE and continue to expand it, mostly because the functional areas within a corporation are siloed and require additional selling, so moving from MNA to strategy, to competitive intelligence, to BD, etc., requires many times a whole new sales cycle. 

Territory Planning is a Phased Process

Sam Jacobs: This sounds like it takes a tremendous amount of work, so two follow up questions. Do you develop it right from the beginning just as you’re hiring the first batch of AEs, but I would think that you phase it in based on milestones that the business hits.

Then what kind of resources do you need as a CRO to enable this level of sophistication in terms of sales op support?

Kiva Kolstein: On the first question you absolutely phase it in, and I think along with everything else like comp plans territories become more complicated over time as you’re required to think about new and different ways to support new folks that you might be bringing in.

Sales and Support Resources to Build This Territory Plan

In terms of the assistance I’d say the two most important hires are sales operations or sales enablement. 

1) Sales operations

Sales ops is my first hire and that person really has to understand, I think most importantly the velocity of opportunities as they move down a funnel, giving us the confidence that the pipeline that we’re creating week over week, month over month will get us to our target at the end of the month or the end of quarter.

2) Sales enablement

The second most important hire is sales enablement. That person also can get involved in customer segmentation and create buyer personas in some of this ABS, ABM strategy alongside sales ops and me. Most importantly, that person is responsible for spinning up or ramping our sellers.


The way I think about sales enablement is that we split it into three parts; the first part being onboarding and that’s usually one to two weeks.

I want that to be Navy Seal style in early, out late, homework every night, presentations to management, really getting you prepared for what life will be like out there on the front lines after your second week is over.

Performance ramp

The second part of sales enablement is what we call performance ramp, so week three to week 15 or week 14, so 12 weeks worth of performance ramp. That is less intense than your first two weeks, but you are still spending significant time with sales enablement and various other folks within the organization mastering different parts of the sales process or getting certified on let’s say discovery, or objection handling, or the deck, or the demo, that kind of thing.

Sales effectiveness

Then the third part is ongoing sales effectiveness. For all of the existing staff that we have on the sales and service team, we want to make sure that they understand how to articulate value, how to talk about ROI. 

Quick-Fire Questions

Sam Jacobs: What I want to do now is shift to some quick-fire questions where we can just get a lay of the land in terms of how you approach different things. Does that sound okay?

Kiva Kolstein: Great, sure.

Sam Jacobs: Great, so first of all big question in the startup land, who should SDRs report to, marketing or sales?

Kiva Kolstein: I’ve seen them report to both. I don’t necessarily have a strong opinion on whether they report to marketing or sales. I do have a strong opinion on making sure that if they report to marketing that marketing and sales are coordinated. 

As long as there’s tight coordination between those two organizations you’re in good shape.

The second thing I have an opinion on is who the SDR ultimately wants to be. It’s thankless, it’s long hours, it’s lots of rejection, difficult to motivate that person to do that job for 12 or 18 months unless they desperately want a career in sales. If they believe they’re growing up in marketing or strategy or some other functional area they may be difficult to motivate in tough times.

Sam Jacobs: Yes makes sense, so monthly, quarterly, or annual quotas? What do you do for AlphaSense?

Kiva Kolstein: Everyone has an annual target, but they’re responsible for achieving each of their quarterly targets and I manage them against a 12 quarter close. If all else fails you need to achieve your annual number. But what tops that is everyone aligning against the quarterly sales goals.

Sam Jacobs: Average quota for SMB reps, mid market, and enterprise?

Kiva Kolstein: I’d say average for SMB is $250,000 to $300,000. Average for mid-market is probably in the neighborhood of $500,000, and the average for enterprise is closer to $900,000. What I’ve learned is you want to be somewhere in the neighborhood of 3X VAEs as OTE in terms of what their target is for the year.

Sam Jacobs: Let’s talk about your tech stack, are you guys a Salesforce shop?

Kiva Kolstein: We are.

Sam Jacobs: What are the other tools that you’re using across sort of your sales technology investment?

Kiva Kolstein: LinkedIn Sales Navigator. We use Outreach and HubSpot—the sellers use Outreach, our marketing team uses HubSpot, our recruiting organization uses Greenhouse to organize candidate interviews and to post new jobs.

Then Slack, I think Slack by far is my favorite app. I’m on Slack all day long, not just with the sales team but with the marketing team, the product team, the finance team, and really everybody. It enables me to connect with people very quickly and ask them quick questions about the deal in the cycle.

Sam Jacobs: Your favorite VP of Sales that’s not you, or just give us a mentor or a leader, people that you brainstorm with as we want to know who are the best people in your ecosystem.

Kiva Kolstein: Mike Zeke, he and I were at GLG for a long time together, then we were on the executive team at Percolate together for three or four years, so we’ve kind of grown-up together in similar environments and I like to bounce ideas off of Zeke.

Then Jess Hunt has been a long time favorite of mine. We worked closely together at GLG for a while and she’s whip-smart, has deep experience managing multiple sides of the business. When I’m really stuck I’ll turn to Jess.

Sam Jacobs: If anybody listening wants to get in touch with you, maybe they’re an incredible account executive or SDR, or they just want to meet up with a coffee, can they and what email address should they use?

Kiva Kolstein: They absolutely can and they can email me at kkolstein@alpha-sense.com

Sam Jacobs: Awesome, Kiva thank you so much for participating and I’ll see you in future meetings with the Revenue Collective.

Kiva Kolstein: Sounds good, thanks so much, Sam.

Sam’s Corner

At the end of every interview that we do we’re going to have a little section called Sam’s Corner where we reflect on what just happened and this is the first Sam’s Corner.

I think we can all agree that that conversation with Kiva was pretty exceptional.

Kiva is such a well respected and well-regarded thought leader in the New York sales community. One of the things that he said at the very beginning was he said, “Make sure that you’re doing what you love.”

My experience is that phrase and that admonition often gets misinterpreted. I think that folks might want to consider a three-circle Venn diagram when they think about their career. The first circle is what you’re interested in, the second circle is what you’re good at, and the third circle is where the market is moving. All three of those circles need to overlap in order to have a successful career.

Don’t Miss Episode 02

To check out the show notes, see upcoming guests, and play more episodes from our incredible lineup of sales leaders, visit gtmnow.com/podcast-subscribe

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Finally, a special thanks again to this month’s sponsor, NodeIf you want to get in touch with me, check my bio for my social handles. I’ll see you next time!

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