Jim Pickering

CRO

Cincinnati, Ohio, United States

About

With over two decades in global enterprise sales leadership, I have consistently driven revenue growth and operational excellence across cybersecurity and SaaS organizations. My career spans pivotal roles at industry leaders such as NetSPI, Swimlane, Infoblox, Fortinet, and Juniper, where I have led high-performing teams, executed strategic go-to-market initiatives, and achieved significant business transformations.  Throughout my career, I have demonstrated a commitment to building scalable sales infrastructures, optimizing organizational structures, and fostering cross-functional collaboration. My expertise lies in aligning sales strategies with long-term business objectives, enhancing forecast accuracy, and driving predictable revenue outcomes. Currently on a professional sabbatical, I am traveling globally with my family, gaining new perspectives and preparing for my next leadership opportunity. I remain engaged in the industry through selective advisory work and am open to exploring roles where I can leverage my experience to drive growth and innovation.

Experience

  • Chief Revenue Officer (CRO) at Swimlane
    Sep 2025 - Present · 11 mos

  • Sabbatical - Open to opportunities, either permanent or fractional, Summer '26 at Sabbatical Career Break
    May 2025 - Sep 2025 · 5 mos

    After a rewarding run in CRO and executive revenue leadership roles, I’ve stepped back for a professional sabbatical to reset, reflect, and reconnect. During this time, I’m traveling around the world with my wife and family — embracing new cultures, perspectives, and likely far too much food and drink! While away, I’m staying close to the industry through selective advisory work and keeping an eye out for the right next chapter.

  • CRO (Fractional/Contract Role) at COFENSE
    Nov 2024 - May 2025 · 7 mos

    Brought on for a 6-month engagement to lead a global sales and GTM transformation. Scope included executing a comprehensive restructuring to align expenses with revenue forecasts, building the company’s strategic 2025 plan, and operationalizing sales processes to drive scalable, data-driven growth. -Strategic Execution: Led a global go-to-market (GTM) restructuring that included a cost-saving reduction in force (RIF) eliminating $3.3M in expenses (36% field sales reduction) and negotiated $300K in annual software savings — all while maintaining growth momentum and hitting key targets. -2025 Planning & Vision: Architected and launched the company’s 2025 GTM plan, aligning the sales org to long-term growth initiatives. Early results: +48% new logo acquisition and +42% expansion growth. -Organizational Optimization: Separated Renewals from New Business Sales, improving ownership, forecasting accuracy, and new logo focus. -Revenue Performance: Exceeded Q1 plan and achieved 90% forecast accuracy across Q4 and Q1. Forecasts upon my departure indicated company was on track to surpass 1H goals for both New Business and Renewals. -Operational Excellence: Designed and implemented critical infrastructure including real-time KPI dashboards, a Capacity Model, and a Propensity Model to drive data-backed decisions. -Territory Realignment: Executed AMS GTM realignment to create balanced coverage and equitable opportunity across the field team. -Sales Process & Enablement: Standardized Quarterly Business Reviews (QBRs) and operating cadence with a new focus on forecast precision and sales accountability. -Messaging & Marketing Collaboration: Partnered with marketing to launch a new “Gold Standard” Sales Presentation — emphasizing our two flagship service offerings: (1) Phishing Detection and Response (PDR) and (2) Security Awareness Training (SAT) to clearly articulate our unique value proposition.

  • EVP, Global Sales at NetSPI
    Feb 2024 - Aug 2024 · 7 mos

    NetSPI is the proactive security solution used to discover, prioritize, and remediate security vulnerabilities of the highest importance, so businesses can protect what matters most. NetSPI secures the most trusted brands on Earth through Penetration Testing as a Service (PTaaS), Attack Surface Management (ASM), and Breach and Attack Simulation (BAS). -Spearheaded the demand funnel engineering project, partnering with board members and cross-functional teams (marketing, sales/rev ops, BDRs) resulting in defining clear KPI objectives across all four demand generation channels to secure the plan -Established foundational operational cadences to include QBR’s, KPI’s and dashboarding for the newly defined funnel objectives -Collaborated with marketing, product mgmt and enablement to amplify our sales presentation -Implemented MEDDPICC to improve forecast predictability and collaborated with enablement teams to onboard the sellers

  • SVP, Worldwide Sales at Swimlane
    Oct 2021 - Jan 2024 · 2 yrs 4 mos

    -Responsible for all aspects of WW Sales, Sales Engineering and Field Operations -Complete transformation of Swimlane’s WW GTM, catapulting ARR 220% and helping to earn Swimlane on the Deloitte Fast 500 two years in a row (38th fastest growing cybersecurity company in 2023) -As an inspirational leader, achieved 94% organizational engagement – highest in the company -As a global operator, re-engineered critical processes including recruiting, employee onboarding/everboarding, compensation plans, gold-standard pitches/demos, operational cadence, sales processes, channel engagement, POV processes, KPI measurement and reporting -Partnered and collaborated with C-suite and leadership teams to solve strategic company challenges -Organized and delivered Swimlane’s most impactful SKOs in company history with a perfect 100 out of 100 rating from the attendees -Assisted my team in negotiating and closing many new logo F/G500 deals across all industry sectors and WW theaters as well as establishing global partnerships with large, global GSI/SP/Consultancies