Sales Role (Type Unspecified)

Overview

You'll be selling 20/20 Insights' strategy-to-execution platform to mission-driven companies. This is performance management software that helps organizations connect strategic goals to day-to-day employee work. At 18 people, this is an early-stage environment where you'll likely be building process as you go.

Role Snapshot

Company Context

Stage: Early-stage (18 employees, funding unknown)

Size: 18 employees

Growth: Actively hiring for sales

Market Position: Small player in crowded performance management/OKR space competing against established platforms

GTM Reality

Pipeline Sources:

• Likely 80%+ outbound - at this size, inbound flow is probably minimal
• You'll be building your own pipeline through cold outreach
• May get some referrals from early customers if product has advocates

SDR/AE Structure: At 18 people total, you're probably self-sourcing or have very limited SDR support

SE Support: Unlikely to have dedicated SEs - you'll do your own demos

Competitive Landscape

Main Competitors: Lattice, 15Five, Betterworks, Culture Amp (performance/goals modules), Workboard, Perdoo

How They Differentiate: Focus on "mission-driven" companies and connecting work to mission/strategy vs pure performance reviews

Common Objections:

• "We already use [Lattice/15Five] for performance management"
• "This seems like another system employees won't use"
• "How is this different from OKR tools we've looked at?"

Win Themes: Deep focus on mission alignment (if selling to values-driven orgs), probably more consultative vs pure software play

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (35%) | Product Demos (15%) | Internal (10%)

Key Activities

• Prospecting mission-driven companies: Researching companies with strong mission/values focus, finding HR leaders and executives, cold outreach via email and LinkedIn. At this stage you're educating a market that may not know they need this.
• Running discovery and demos: You'll do your own product demos since there's likely no SE team. Expect to spend time understanding their current performance process, strategic planning approach, and pain points with alignment.
• Multi-threading deals: Selling performance management means talking to HR, but also looping in executives who care about strategy execution. You'll be coordinating across multiple stakeholders.
• Managing long sales cycles: HR tech sales take months. You'll spend a lot of time following up, waiting for budget approval, competing with other priorities, and dealing with deals that go quiet.

The Honest Reality

What's Hard

• Performance management is a crowded, noisy category. Most prospects already have something (even if it's just spreadsheets) and changing behavior is hard.
• At 18 people, you're selling against established brands with bigger marketing budgets and more social proof. You'll hear "can you send me case studies" a lot.
• "Mission-driven companies" is a positioning, but you'll need to figure out who that actually is and how to find them at scale.
• Long sales cycles with multiple stakeholders mean lots of deals in "evaluation" limbo. Budget gets pulled, priorities shift, projects get tabled.
• Small company means you're figuring out messaging, pricing, ideal customer profile as you go - less playbook, more experimentation.

What Success Looks Like

• Closing 1-2 deals per quarter in early months, ramping to 3-4 as you figure out who converts
• Building a repeatable outbound motion that generates consistent pipeline
• Finding 2-3 customer stories you can use to sell the next deal

Who You're Selling To

Primary Buyers:

• VP/Director of People/HR at 100-1000 person companies
• CEOs/COOs at mission-driven organizations (nonprofits, B Corps, purpose-driven startups)

What They Care About:

• Employee engagement and retention (can you prove this helps?)
• Actually executing on strategic plans vs having them sit in decks
• Making performance reviews less painful and more meaningful
• Getting leadership visibility into what teams are working on
• ROI is often soft (engagement, alignment) vs hard savings

Requirements

• Experience selling B2B software, ideally HR tech or workflow/productivity tools
• Comfortable with full-cycle sales - prospecting through close
• Ability to run your own demos and learn product deeply
• Experience selling into HR or people ops teams preferred
• Comfortable in early-stage environment with ambiguity and changing process
• Self-starter who can build pipeline without heavy SDR support