Thomas Grimshaw

Senior Advisor to Executives. I sell the way I buy. Through trusted relationships.

United States

About

I sell the way I buy. Through trusted relationships. My clients are senior executives - founders, CEOs, and global leaders navigating significant decisions in markets they are still getting to know. Most of them find me the same way: through someone they already trust. I've lived and worked across Boston, New York, San Francisco, London, and Spain. I know what it means to land somewhere new at a senior level - the questions you don't know to ask yet, the things that matter more than you expect, and the ones that matter less. That experience shapes how I work with clients who are arriving somewhere for the first time with high expectations and limited bandwidth. In Miami, Boston, New York, Naples, and across every market where I have lived myself, I operate at the top of the market. Not by volume. By relationship. Discretion is not something I advertise. It is simply how I work. If we're connected, it's because someone whose judgment you respect thought the introduction was worth making. I don't take that lightly.

Experience

  • Founder & Principal Advisor at TGRE (Real) | Compass
    Nov 2019 - Present · 6 yrs 8 mos

    Founded and scaled a multi-market real estate advisory practice across Massachusetts and South Florida, operating first on the Compass platform and subsequently on the Real infrastructure as TGRE. The business was built and run as a full sales organization — with self-defined revenue targets, a referral-driven pipeline, CRM-managed follow-up systems, and a team of agents I hired, trained, and coached to performance. • Player-coach leadership: maintained a personal book of business while building and leading a multi-agent team, with direct accountability for both individual production and team results • $50M+ in closed sales volume with 90%+ of revenue generated through repeat clients and referral relationships, a metric that reflects trust-based selling, not transactional volume • Closed $12M+ in off-market transactions by sourcing and connecting motivated buyers and sellers outside traditional channels. • Set and exceeded revenue targets each year with full P&L ownership, quota accountability • Built and managed CRM workflows, structured follow-up cadences, and pipeline forecasting • Recruited and onboarded agents across markets; developed training programs around consultative selling, objection handling, and client experience • Operated in an AI-forward manner across business development, market research, client communication, and pipeline management, an early adopter with documented productivity gains • Maintained location-agnostic operations across four markets simultaneously through systems, delegation, and disciplined communication

  • Enterprise Sales Executive at Final Offer
    Jul 2024 - Dec 2025 · 1 yr 6 mos

    Drove enterprise adoption of a PropTech SaaS platform by building relationships with brokerage leaders, team leads, and top-producing agents across the U.S. and Canada. Combined real estate market credibility with a consultative SaaS sales motion to open doors that pure-tech reps could not. • Delivered 20% revenue growth by closing high-value contracts with brokerage leaders and high-volume agent teams • Built and managed a multi-market pipeline from prospecting through close, navigating complex stakeholder environments at the ownership and C-suite level • Collaborated with product and leadership teams to sharpen messaging, refine ICP, and improve go-to-market targeting — contributed directly to positioning iteration • Leveraged deep real estate domain expertise to accelerate trust with prospects and compress sales cycles • Operated as an early-stage sales contributor, balancing outbound development with strategic account management in a resource-constrained environment

  • Sr. Enterprise Relationship Manager - Sales Solutions at LinkedIn
    Nov 2018 - Nov 2019 · 1 yr 1 mo

    Managed a portfolio of 25+ of LinkedIn's most strategic enterprise accounts with a $4M individual quota, serving as a trusted advisor to C-level executives and sales leaders on the Sales Navigator platform. Focused on seat retention, expansion, and embedding modern social selling into client-facing sales cultures. • Achieved 100% seat retention and renewal across the portfolio; doubled contract size on first renewal within 30 days — Live Nation • Drove measurable expansion in previously stagnant accounts through in-person executive engagement and hands-on team coaching and enablement • Built award-winning cross-functional partnerships with CSM, AE, BDR, and SME counterparts to protect and grow at-risk accounts • Featured speaker at global SKOs for American Airlines, Live Nation, and ComData — delivered training on modern social selling strategy • Certified Rock Your Profile coach and trainer; developed and delivered enablement programming to client sales teams

  • Sabbatical & Professional Development at Sabbatical
    2015 - 2017 · 2 yrs

    Took a deliberate sabbatical to invest in long-term professional development, personal clarity, and leadership capability. Pursued advanced coaching certification through NYU, completed international immersive travel including an extended residency in Spain, and continued active real estate advisory work throughout. • Earned advanced coaching certification from NYU, developed frameworks for sales performance, leadership mindset, and sustainable execution that have been applied across all subsequent roles • International residency in Spain: developed cross-cultural communication, adaptability, and a working fluency in navigating unfamiliar environments, skills that transfer directly to complex, global enterprise selling • Returned to full-time sales roles with a sharper sense of strategic prioritization and executive presence

  • Sales Director, Global Special Features, Branded Content at The Wall Street Journal
    2014 - 2015 · 1 yr

    Led revenue growth for custom content and integrated media solutions across digital, print, and mobile platforms. - Exceeded $12M sales goal by 20% - Closed $1M multi-platform deal with a dormant client - Sold $800K integrated campaign across digital, print, and social