Jake Cronin

Account Executive

Siro

Account ExecutiveOutbound HeavyConsultativeRemote📍 Remote
Deal Size: $30-80K ACV
Sales Cycle: 4-8 weeks
Posted by Jake Cronin

Overview

You're selling AI conversation intelligence software to companies that do in-person sales - auto dealerships, home improvement contractors, HVAC installers, real estate agencies, medical device reps. These buyers have never had a "Gong for in-person" before, so you're educating a new market while competing against "do nothing." Full-cycle role: you find the leads, run the demos, negotiate the deals, and close them yourself.


Role Snapshot

AspectDetails
Role TypeFull-cycle AE (prospect to close)
Sales MotionOutbound-heavy with some inbound
Deal ComplexityConsultative
Sales Cycle4-8 weeks
Deal Size$30-80K ACV (estimated)
Quota (est.)$1.2-1.5M in bookings/year ($100-125K/month)

Company Context

Stage: Series A/B (estimated - 93 employees, aggressive hiring, strong PMF signals)

Size: 93 employees

Growth: Hiring 5 AEs in 5 weeks, ranked #3 on RepVue, describes "crazy product-market fit"

Market Position: Category creator - first conversation intelligence platform built specifically for in-person sales interactions


GTM Reality

Pipeline Sources:

  • 30% Inbound - some traffic from brand awareness, CEO active on LinkedIn, demo requests from website
  • 70% Outbound - you're building your own pipeline through cold outreach, industry events, targeted prospecting into verticals
  • Partners/Referrals - early stage, not a major source yet

SDR/AE Structure: Self-sourcing model - you hunt your own deals. No dedicated SDR support mentioned, which is typical at this stage.

SE Support: Unclear - likely shared pool or you handle technical demos yourself given the product is relatively straightforward (mobile app + dashboard)


Competitive Landscape

Main Competitors:

  • "Do nothing" (biggest competitor - these teams have never bought this type of software)
  • Legacy call recording tools that don't handle in-person conversations
  • Generic conversation intelligence platforms built for remote sales (Gong, Chorus) that don't work for face-to-face

How They Differentiate: Only platform purpose-built for in-person sales conversations. Captures audio in real environments (showrooms, job sites, homes), analyzes interactions that happen face-to-face.

Common Objections:

  • "Our reps won't want to be recorded"
  • "We already coach our people, we don't need software"
  • "Sounds expensive for what it does"
  • "How does this work in a noisy environment?" (technical proof point needed)

Win Themes:

  • First time sales managers can actually hear what's happening in the field
  • Turn top performers' conversations into training for everyone else
  • Catch deals slipping through cracks (missed follow-ups, objections not handled)

What You'll Actually Do

Time Breakdown

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

Key Activities

  • Cold outreach to VP Sales / Sales Directors: You're identifying companies with 20+ person in-person sales teams (auto groups, HVAC franchises, home builder sales offices) and reaching out cold via LinkedIn, email, and phone. Response rates are low because this is a new category - plan on 100+ touches per week.

  • Discovery calls and demos: You walk prospects through how the mobile app captures conversations, how the AI surfaces coaching moments, and show them dashboards with actual talk tracks and conversion insights. Demos are 30-45 minutes. You're doing 8-12 of these per week when ramped.

  • Multi-threading deals: Most deals need buy-in from Sales Leader + Operations + sometimes IT (for mobile device management). You're scheduling follow-ups, sending ROI calculators, and chasing people for next steps. Deals stall when priorities shift or budget freezes.

  • Closing and negotiating: You handle all contract discussions, pricing negotiations, and close the deal yourself. Legal review can add 2-3 weeks. You're trying to close 2-3 deals per month when fully ramped.


The Honest Reality

What's Hard

  • You're creating a category: Most prospects have never thought about recording in-person conversations. You spend a lot of time explaining why this matters before you can even pitch the product. Many conversations end with "interesting, but not a priority right now."

  • Self-sourcing everything: No SDR handing you qualified meetings. You're building your own list, doing your own outreach, and managing your own pipeline top-to-bottom. If you don't prospect consistently, your pipeline dries up in 6-8 weeks.

  • Proving ROI is fuzzy: Hard to quantify value before they use it. You're selling on faith that conversation intelligence will improve close rates and coaching effectiveness, but you can't show a payback calculator like you could with cost-saving software.

  • Fast hiring environment: They want 5 AEs in 5 weeks. That means onboarding, playbook, and process are still being figured out. You'll need to be comfortable with ambiguity and building as you go.

What Success Looks Like

  • Booking 8-12 qualified discovery calls per week through your own outreach
  • Maintaining 25-30 active opportunities in pipeline with realistic close dates
  • Closing $100-125K in new bookings per month (2-3 deals)
  • 30-40% demo-to-close rate after 6 months in the role

Who You're Selling To

Primary Buyers:

  • VP of Sales / Sales Directors at mid-market companies ($50-500M revenue)
  • General Managers of dealership groups, franchise operators, regional sales leaders
  • Revenue Operations leaders at larger orgs looking for field sales visibility

What They Care About:

  • "How do I know what my reps are actually saying in the field?"
  • Improving conversion rates (test drive to sale, estimate to contract, demo to close)
  • Scaling coaching without riding along on every sales call
  • Capturing tribal knowledge from top performers before they leave
  • Proving to execs that sales training investments are working

Requirements

  • 3-5 years full-cycle B2B SaaS sales experience - you've sourced and closed your own deals before
  • Comfortable with high outbound volume - you're not sitting around waiting for leads to come in
  • Can handle ambiguity and fast growth - playbooks aren't fully baked, you'll help build them
  • Willing to grind through category creation - most people won't immediately understand why they need this
  • Track record of hitting quota in a self-sourced environment
  • Bonus: Experience selling to sales leaders or operations teams, or background in retail/field sales industries