Hayden Willoughby

Sales Representative

CultureSpace

Account ExecutiveOutbound HeavyConsultative
Deal Size: $50K-500K per project
Sales Cycle: 3-9 months
Posted by Hayden Willoughby•

Overview

You sell office furniture and workspace design solutions—desks, demountable walls, acoustic panels, collaborative spaces—to companies doing office redesigns or expansions. You're working deals that range from $50K for a single floor refresh to $500K+ for full office buildouts. Most of your time is spent prospecting into commercial real estate triggers, running site visits, coordinating with your design team on proposals, and navigating multi-stakeholder approval processes.


Role Snapshot

AspectDetails
Role TypeFull-cycle AE (prospect to close)
Sales MotionOutbound-heavy with some referral business
Deal ComplexityConsultative to Enterprise
Sales Cycle3-9 months (depends on project scope and approval layers)
Deal Size$50K-500K+ per project
Quota (est.)$800K-1.5M annually

Company Context

Stage: Private, bootstrapped or early-stage (77 employees)

Size: 77 employees

Growth: Small player in a fragmented market dominated by Herman Miller, Steelcase, Knoll

Market Position: Challenger competing on customization and culture-alignment messaging vs big box furniture suppliers


GTM Reality

Pipeline Sources:

  • 70% Outbound - Cold calling facilities directors, HR VPs, and office managers at companies with recent funding, office expansions, or lease renewals. You're tracking commercial real estate news and growth indicators.
  • 20% Referrals - From architects, commercial real estate brokers, and existing clients
  • 10% Inbound - Website inquiries (sporadic, usually tire-kickers)

SDR/AE Structure: No dedicated SDRs. You're doing all your own prospecting.

Design Support: Internal design team creates renderings and proposals, but you're coordinating the entire process.


Competitive Landscape

Main Competitors: Herman Miller, Steelcase, Knoll, WeWork Workplace (for larger deals), local/regional furniture dealers

How They Differentiate: "Culture-driven" positioning—customization and alignment with company values vs cookie-cutter catalogs. Likely competing on service and flexibility since they can't match big players on price or brand.

Common Objections: "We already work with [Herman Miller/Steelcase]", "Your price is 20% higher than our current vendor", "We need to see more case studies in our industry", "Can you match their lead times?"

Win Themes: Design flexibility, white-glove service, understanding company culture, faster customization than enterprise vendors


What You'll Actually Do

Time Breakdown

Prospecting (35%) | Active Deals (40%) | Proposals/Internal (25%)

Key Activities

  • Outbound Prospecting: 30-40 calls/emails per day to facilities managers and HR leaders. You're looking for office expansion triggers—new funding rounds, lease renewals, return-to-office mandates, acquisitions. Most ignore you.
  • Site Visits: Walking client offices with a tape measure and iPad, taking photos, asking about workflow and collaboration needs. These are 1-2 hour commitments plus travel time.
  • Proposal Coordination: Working with your internal design team to create 3D renderings and quotes. Lots of back-and-forth as client requirements change. Each proposal takes 8-15 hours of work.
  • Multi-Stakeholder Navigation: Presenting to facilities, HR, finance, and executive teams. Getting budget approval means looping in CFOs and justifying ROI on "culture-driven" furniture vs cheaper alternatives.
  • Project Management: Once deals close, you're coordinating delivery, installation, and punch lists. This pulls you away from selling but keeps clients happy for future expansion projects.

The Honest Reality

What's Hard

  • Long sales cycles with lots of stalls. Projects get delayed because of budget freezes, office lease uncertainty, or leadership changes. Your Q4 pipeline will slip to Q1 constantly.
  • You're fighting uphill against established vendor relationships. Facilities managers have worked with Herman Miller for 10 years—you need to prove you're worth the switching cost.
  • Deals are lumpy. You might close $200K in one month and $0 the next three months. Feast or famine.
  • You're stuck in the middle of client-design team-installation coordination. When installation goes wrong (and it will), you're the one getting the angry calls.
  • Price pressure is constant. You're competing against massive vendors with better purchasing power. Clients want your service at their prices.

What Success Looks Like

  • Closing 8-12 projects per year in the $50-150K range with 1-2 larger projects ($200K+) annually
  • Building a referral engine with commercial real estate brokers and architects who feed you deals
  • Getting second and third projects from existing clients as they expand to new floors or locations

Who You're Selling To

Primary Buyers:

  • Facilities Directors/Managers (day-to-day contact, care about functionality and timelines)
  • HR/People Ops VPs (care about employee experience and culture fit)
  • CFOs or Controllers (final budget approval, care about cost per seat and ROI)

What They Care About:

  • Lead times: Can you deliver before their lease starts or office opening?
  • Total cost: Not just furniture price, but installation, project management, warranty
  • Flexibility: Can you adapt designs as their headcount projections change?
  • Proven results: Case studies from similar companies (they want to see you've done this before)
  • Service: Will you handle installation headaches or disappear after the sale?

Requirements

  • 2-4 years in B2B sales, ideally in commercial furniture, office design, construction, or commercial real estate
  • Comfort with long, consultative sales cycles and staying organized across 15-25 active opportunities
  • Ability to read floor plans and discuss spatial design (you'll learn this, but technical aptitude helps)
  • Strong project management skills—you're juggling design timelines, client changes, and installation logistics
  • Resilience with rejection and deal slippage—most of your outreach goes nowhere and deals take forever
  • Willingness to do site visits and occasional travel to client offices
  • Proficiency with CRM (Salesforce/HubSpot) and design tools (you'll use software to show clients renderings)