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7 Phases of Hiring That Took Outreach From $0 to $230M

How the sales leader's role, early hires, capacity hiring and second-line managers change at each stage of growth

Mark Kosoglow · Operator AI

Published September 6, 2024
About this resource
Format
SaaSOpen 2024 NYC
Length
21 min video
Inside
8 key moments
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What you’ll learn

Mark Kosoglow traces the hiring phases that took Outreach from its first sales team to organizational scale. He explains the changing expectations of leaders, early hires, capacity hiring, and culture-preserving second-line management.

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Key moments

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Set expectations and evaluate mental models

“allowed us to then spring up to those other areas and I went from the person that was the fixer and the implementer to a person that did three things I clearly communicated my expectations I clearly communicated the timeline on which I needed those expectations to be met and I evaluated the mental model by which people created solutions to create those outcomes and when I did that that's when I went from being a VP or whatever to an executive and I felt like I was really helping Outreach again so”

Make early hires capable team builders

“within his second year at being at Outreach I hired a guy that sold cleaning services and cleaned Banks and you know what he turned out to be one of the Outreach Legends too so you know you have to make sure that your first team is cohesive and probably I would say maybe necessarily linked to the leader that's hiring them in some other way and some kind of relationship if your first hire can't hire their first team of people they know you probably don't have your right first hire so we got to two and a half million and then we went to”

Hire for the company you actually have

“first time we hired for capacity we didn't really know what kind of rep we needed and we hired all wrong you know what I thought I needed reps that were number one at good brands that knew how to sell you know I figured out didn't work people that were at number one at good brands that knew how to sell and you know why is because Outreach wasn't a brand it was a nothing it was just an a movement and what I did is is I looked at my best sellers and you know what they were they were evangelists they were John the Baptist they had honey and”

Build through second-line leaders

“people coming in the office my strategic leader hired remote but you know what if you went from one team to the next it still felt familiar it was just a little different and so building an organization and hiring for an organization is about hiring those second line leaders those directors those VPS however you structure it that can help build on the foundational culture that you're already in and that's how you build an organization otherwise what you end up is you build out organizations and there's different whole these little thief Dums where”

Track Outreach revenue growth

“👷🏻‍♀️ 📐 🩺 🏛️ 🗣️ Outreach Revenue Growth”

Hire to form the first team

“Outreach Revenue Growth Hire to form the first team Sales leader role:👷‍♀️Doer -> 📐 Builder 2015 - $2.5M”

Hire to create capacity

“Outreach Revenue Growth Hire to create capacity Sales leader role: 📐 Builder -> 🩺 Doctor 2017- $25M”

Hire to build an organization

“Outreach Revenue Growth Hire to build an organization Sales leader role: 🏛️ Architect 2019- $85M”

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  • 7 Phases of Hiring That Took Outreach From $0 to $230M - Slide Deck

About the speaker
Mark Kosoglow

Mark Kosoglow

CEO · Operator AI

Co-founder & CEO of Operator AI, an AI-driven platform helping sales teams analyze and optimize their performance.

Company revenue
$2M

Slide by slide

Each slide with a short explanation of what it shows. Open the slide text for its exact wording.

11 passages

Seven phases of hiring

  1. Slide text

    SaaSOpen, September 2024 7 Phases of Hiring That Took Outreach From$0 to $230M And how your sales leader should grow with their org so you don’t have to fire them Mark Kosoglow CEO, Operator

  2. Outreach grew from $250K to $230M ARR

    The chart traces Outreach ARR from $250K in 2014 to $230M in 2022, with each year adding a larger increment. The rising slope frames the talk’s focus on how leadership roles change as a company scales.

    Slide text

    Outreach Revenue Growth

Outreach revenue growth

  1. Growth changes the founder’s role

    An ascending curve maps seven revenue stages to shifts from doing the work toward building and leading an organization. The people icons emphasize that growth brings a series of role changes, not one permanent leadership mode.

    Slide text

    👷🏻‍♀️ 📐 🩺 🏛️ 🗣️ Outreach Revenue Growth

  2. At $250K, lead by doing

    At the first stage, the founder is still the first leader and doer. The curve places this phase at $250K ARR, where hands-on work anchors early growth.

    Slide text

    Outreach Revenue Growth Hire to get the first Sales leader role: 👷‍♀️Doer 2014 - $250k

Forming the first team

  1. At $2.5M, build the team

    At $2.5M ARR, the founder shifts from individual doer toward team builder. The photo and phase marker show the transition from personally executing work to creating capacity through others.

    Slide text

    Outreach Revenue Growth Hire to form the first team Sales leader role:👷‍♀️Doer -> 📐 Builder 2015 - $2.5M

  2. At $10M, stop carrying every task

    At $10M ARR, the founder is urged to stop trying to handle everything and focus on building the team. The phase marker places this pressure point before the company adds more scale.

    Slide text

    Outreach Revenue Growth Hire to stop cries for mercy Sales leader role: 📐 Builder 2016- $10M

Creating capacity

  1. At $25M, create capacity

    At $25M ARR, the founder’s role moves from builder toward doctor, diagnosing organizational needs and creating room for the company to grow. The curve links this shift to a new phase of scale.

    Slide text

    Outreach Revenue Growth Hire to create capacity Sales leader role: 📐 Builder -> 🩺 Doctor 2017- $25M

  2. At $50M, catch the organization up

    At $50M ARR, the company must catch its organization up with its growth. The founder shifts from diagnosing issues toward architecting a structure that can support the larger business.

    Slide text

    Outreach Revenue Growth Hire to catch back up Sales leader role: 🩺 Doctor -> 🏛️ Architect 2018- $50M

Building an organization

  1. At $85M, build the organization

    At $85M ARR, the founder’s work centers on building the organization. The stage illustration marks this as the architect phase, focused on the company’s structure rather than individual execution.

    Slide text

    Outreach Revenue Growth Hire to build an organization Sales leader role: 🏛️ Architect 2019- $85M

  2. At $125M, move upmarket

    At $125M ARR, the founder is encouraged to move upmarket and transition from architect toward communicator. The curve ties this leadership change to the company’s next growth stage.

    Slide text

    Outreach Revenue Growth Hire to go upmarket Sales leader role: 🏛️ Architect -> 🗣️ Communicator 2020- $125M

  3. Closing contact details

    The speaker closes by thanking the audience and inviting follow-up through the contact details shown on the slide.

    Slide text

    SaaSOpen, September 2024 Thank you! [redacted email] Mark Kosoglow CEO, Operator