Michael S.

Chief Revenue Officer, GTM Advisor, Ai Conductor

San Francisco Bay Area

About

I build revenue organizations in environments where the path is not clean, the market is moving, and the margin for error is real. My experience has been earned scaling companies through ambiguity, from early traction to meaningful ARR, while navigating changing products, evolving ICPs, complex enterprise buyers, and the operational realities that come with growth. I have led revenue teams across inside, corporate, and enterprise motions, owned forecasting and P&L accountability, and partnered closely with product, finance, and executive leadership to build systems that hold up under pressure, not just in good quarters. What I bring is judgment. Knowing when to push, when to simplify, and when to make the hard call that protects the long term business. Areas of focus include: • Scaling revenue from $0 to $50M+ ARR • Enterprise GTM strategy and complex deal execution • Building and leading high performing sales teams • Forecasting rigor, incentive design, and accountability • Navigating growth while preserving trust, culture, and market credibility I believe strong teams are built through trust, clear expectations, and shared ownership of outcomes.

Experience

  • Parkade (9 mos)
    • Chief Revenue Officer
      Apr 2026 - Present · 4 mos

      Parkade is a SaaS platform that automates parking operations for multifamily residential communities. It integrates directly with property management systems to handle management, payments, enforcement, and gate access through a single mobile-connected platform. Customers include Greystar, Milhaus, and FirstService. As Chief Revenue Officer, I own net new revenue from pipeline generation through close, leading both sales and marketing.

    • Strategic Advisor
      Nov 2025 - Apr 2026 · 6 mos

  • Founder at Clear Signal Advisory
    Apr 2025 - Present · 1 yr 4 mos

    Clear Signal Advisory provides GTM and sales advisory for CEOs, founders, and revenue leaders at B2B SaaS companies from Seed through Series C.

  • Chief Sales Officer at Workera
    Jul 2024 - Jan 2026 · 1 yr 7 mos

    Workera, backed by NEA, Jump Capital, Owl Ventures, and Andrew Ng’s AI Fund, is the Workforce Transformation Platform redefining how enterprises objectively understand where their teams are, define their ideal future state, and close their gaps. Workera’s Workforce Transformation Platform comprises a suite of products to help enterprises align skills to business goals, measure the capabilities of their teams, develop employees in relevant skills, and mobilize the workforce effectively. Our vision is to enable humanity to achieve its fullest potential and accelerate progress. Join the skills-based revolution!

  • Advisor & Fractional CRO at Darc Networks
    Jul 2024 - Jun 2025 · 1 yr

  • SVP of Sales at Forethought
    Jan 2023 - Feb 2024 · 1 yr 2 mos

    Launched in 2018, Forethought (acquired by Zendesk) is a leading generative AI company providing customer service automation that helps support teams maximize efficiency and productivity. Forethought’s products enable seamless customer experiences by infusing generative AI, powered by Large Language Models (LLMs), at each stage of the customer support journey: resolving common cases instantly, predicting and prioritizing cases, and assisting agents with relevant knowledge—all from one platform.