Steven Brady

Sailing your startup ship to more revenue, FAST

"Your first 50 employees must be pirates or romantics. And you can’t build a startup with normal people. It’ll fail. " - Jason Lemkin.

Years ago startups were only for the quirky, and as a sales leader and operator with 10+ years experience in startups at seed, Series A, and Series B, I am the quirkiest sales pirate you'll ever meet.

My experience is predominantly B2B in a variety of SaaS and Fintech with a focus on the SMB and Mid Market segments. I'm world-class at building the foundational sale…

Steven Brady




    Interseller helps recruiters find and make contact with candidates by finding their email and sending email sequences


  • Keep Technologies

    Keep Technologies

    Founding team - Sales Lead

    Apr 2022 - May 2023

    Keep offers a checking account and credit card for Canadian SMBs. Businesses get better cashback rewards on card spend, lower domestic and international wire fees, currency conversion at a fair price, and increased credit limits for working capital needs.

    • Keep is building the Brex + Mercury Bank for cross-border businesses in Canada.
    • Hired by CEO as the first Sales Lead (executive position) and my responsibilities included all things go-to-market. Oversaw tremendous customer and revenue growth during the first year, leading to a $10m+ funding round from a top-tier VC in the worst startup fundraising environment in decades.
    • Learned just how awful (yet profitable) Canadian banks are to their business clients and reinforced my belief that Canadians are the nicest people on the planet.



    Jan 2022 - Jan 2023

    HYPCCCYCL [haɪpˈsaɪk(ə)l] is a challenger community of over 15,000 innovative C-Levels & VPs from the likes of Cisco, Okta, Salesforce, DocuSign, Gong, and many more

    • HYPCCCYCL is an invite-only, professional community where top B2B revenue leaders cross-train their GTM skills with VCs
  • G2i Inc.

    G2i Inc.

    Director Of Business Development (fractional)

    Jan 2021 - Dec 2021

    G2i is the only hiring platform that puts developer health first. We connect qualified developers with incredible companies committed to improving developers' mental, physical, and emotional health and well-being. This approach begins with providing developers and clients with a transparent hiring process. Companies get access to in-depth, performance-ranked developer profiles through our deep vetting process, technical interviews, as well as cultural and language assessments.G2i focuses on vetting and serving clients that support the developer health mission — leveraging our expertise to match individuals with work environments that improve their health, support recovery from burnout, and enable professional growth through restful work. More information about our mission and commitment to developers and clients can be found on or follow us on Twitter @g2i_co.

    • Designed and executed SDR function, including prospecting processes, enablement stack, comp plans, and interview/hiring plan
    • Hired, trained, and managed two SDRs
    • Created and lead initial "candidate marketing" function to leverage outbound processes for sourcing and onboarding new engineering talent
    • Assisted with hiring and onboarding VP of Sales replacement
  • Pavilion



    Dec 2020 - Dec 2022

    Pavilion is powered by an international community of sales, marketing, RevOps, and success leaders from the world’s fastest growing companies. Together, we teach new skills, forge meaningful connections, and help our companies grow. Unlock your professional potential and level up with community-powered learning for CEOs, GTM leaders, and teams. Join today at

    • Pavilion (formerly The Revenue Collective) is a private, invitation-only organization exclusively for top sales, marketing, and operations leaders and executives worldwide.
  • Modern Sales Pros

    Modern Sales Pros


    Feb 2019 - Dec 2022

    35,000+ members, 6k+ companies, invite-only peer learning community focused on sales leadership, sales management, sales operations, and sales enablement roles from the best revenue organizations. Modern Sales requires a high-rigor, highly-analytical, and technically-competent approach to selling, in order to support high-velocity, high-complexity sales opportunities. The goal of MSP is to accelerate the learning and professional development of exemplars of this school of selling through peer education and provide an extremely high-quality environment to ensure that those aims are achieved. Ready to level up your sales excellence? To show you how much we care about furthering your sales management education, we're sending sales managers, leaders, ops, and enablement professionals free copies of "Founding Sales" written by MSP's Founder Pete Kazanjy. Get your copy, no catch, no ask:

    • Modern Sales Pros is the world's largest community for leaders in sales, operations, enablement and related disciplines. Our mission is to help our community learn how to solve the biggest challenges they face (and would otherwise bang their head against the wall trying to solve). Our 13,000 members learn from each other through our online message board and through amazing in-person events.
  • Interseller


    Head of Sales

    Oct 2017 - Nov 2020

    • Acquired by Greenhouse October 2021
    • 1️⃣ Employee #1
    • 👨‍👩‍👧‍👦 Scaled revenue org from 1 to 8
    • 🏦 Responsible for all revenue and GTM functions
    • 📈 Increased paying users from 100 -> 1500+
    • ...all with only one pre-seed funding round 😎
  • Square


    Account Executive

    Mar 2015 - Oct 2017

    Invent today. Shape tomorrow.

    • Working to make commerce easy.
    • IPO (Nov '15) that was cool.
  • ShopKeep POS

    ShopKeep POS

    Account Executive

    Aug 2013 - Feb 2015

    Powering the businesses that are the backbone of the global economy, Lightspeed’s one-stop commerce platform helps merchants innovate to simplify, scale and provide exceptional customer experiences.

    • ShopKeep POS, a fast growing company based in New York City, provides cloud-based point-of-sale software that helps retail shops and restaurants make smarter decisions that grow their business. Founded and designed by a merchant, our mission is to be an advocate for retailers, helping to make it simpler to start and run a successful business.
  • SinglePlatform


    Account Executive

    Jan 2013 - Jul 2013

    Since being founded in 2010, SinglePlatform has been helping local businesses get new customers by enabling them to publish their most important information everywhere consumers are making decisions online. Over 40,000 businesses rely on SinglePlatform everyday to showcase and update their menus, products, and services on the web's most popular sites and apps, all from one place. After being named one of the most promising startups in America, SinglePlatform was acquired and joined the Constant Contact family in June 2012. Visit for more information.

    • Evangelized and educated SMB owners on the SinglePlatform products, services, and tools that improve visibility for small business through leveraging mobile technology and hyper local search. Guided customers through the tools and techniques best suited for their needs while consistently demonstrating the importance and value of digital store front management and mobile search.

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