Sales Support for Lean Teams
You’re already selling. Now let’s make every conversation count. For founders, solo sellers, and small teams navigating long B2B sales cycles, complex buyers, and the leap to larger deal sizes.
Hi–I'm Tasha Roberts
I help B2B tech and software companies navigate complex sales and unlock growth: long sales cycles, multi-stakeholder buying teams, and the shift from founder-led selling to scalable revenue.With 20 years in enterprise and technical sales, I bring a mix of strategic advisory, coaching, and hands-on support to help teams apply what works in real time. My work spans Canada, the U.S., and Europe, offering insight into how buying behaviour and growth strategies play out across markets.I founded topiary in 2015 to support growing companies with strong products but stalled sales. Since then, I’ve helped founders and teams refine positioning, strengthen strategy, and build habits that support sustainable growth.At the core, my work connects:
● Positioning – how you connect your value to what your buyers care about● Buyer journey – how your customers decide and what they need along the way● Sales execution – how you move deals forward with clarity and purposeI don’t rely on pressure or pitch-heavy tactics. I help teams guide conversations that build trust, align with decision-making, and reinforce value at every step.Curious how we might work together?
🚀 Making the Shift to Bigger Deals
Selling into $15K–$200K+ ARR deals? Your sales approach needs to grow with you.This shift isn’t just about pitching bigger numbers. It’s about building trust, navigating complex decision dynamics, and sustaining momentum over a longer cycle.Bigger B2B deals require consistency across your sales process and how you engage throughout the buyer journey. You’re not convincing one person. You’re equipping a team of stakeholders to confidently choose and champion your solution.Whether you're deep in active deals or ready to strengthen your foundation, there are two ways we can work together.👇
01 Sales Growth Insight
A structured review of your current sales approach, designed to help you grow into larger, more strategic deals with a process that scales.This four-session diagnostic helps you step back and evaluate how you currently sell. We'll take a close look at your systems, sales habits, and deal flow to uncover gaps, opportunities, and patterns that either support or hold back your ability to win larger, more complex deals.Whether you're refining your sales approach today or preparing to grow your team, this series helps you build a stronger foundation for strategic growth.
Curious but not sure if it's the right fit? Start with a 30-minute call to explore whether this series makes sense for you.
02 Pipeline Review and Deal Strategy Series
Learn by doing. We work on active deals in your sales pipeline, and the insights you gain will shape how you approach future deals. Get an experienced outside perspective and move forward with more clarity and confidence. Together, we’ll review what’s working, uncover hidden blockers, and refine how you move strategic deals forward.What You Get📅 Session 1: Pipeline Review
We look at your current sales pipeline to see what's moving, what's stalled, and where momentum is missing. You'll leave with a clear picture of which deals to focus on and why.📅 Sessions 2–4: Targeted Deal Strategy
Work through 1–2 deals per session to shape strategies you can apply immediately and carry forward into future deals.You’ll work on:● Understanding and aligning with buyers across the deal● Spotting and closing stakeholder gaps● Working through buyer hesitations● Clarifying messaging and planning next steps that help move the deal forwardThis is live work on real deals.✅ This Is For You If...● You’re a solo seller, founder in the trenches, or part of a lean team● You’re unsure how to progress a deal forward●You’re selling into complex organizations or longer cycles● You want better structure and sharper decision-making● You're curious about blind spots in your sales process and approach
Curious but not sure if it's the right fit? Start with a 30-minute call to explore whether this series makes sense for you.
Thank You
I'm looking forward to meeting you and learning more about what you're working on.