Kyle Hollingsworth

Sales Development Representative

Giga

SDROutbound HeavyTransactional
Sales Cycle: 1-3 weeks (to book qualified meeting)
Posted by Kyle Hollingsworth

Overview

You're booking meetings for Account Executives by cold calling and emailing customer support VPs, operations leaders, and CX directors at mid-market and enterprise companies. You're selling them on taking a demo of Giga's AI voice agent platform - essentially pitching AI that handles customer support calls at scale. Most of your day is outbound prospecting into companies that handle high call volumes (telecom, insurance, retail, SaaS).


Role Snapshot

AspectDetails
Role TypePure SDR - booking meetings only
Sales MotionOutbound-heavy (95%+)
Deal ComplexityTransactional (your job is to book the meeting)
Sales CycleYour part: 1-3 weeks to book a qualified demo
Deal SizeN/A (you don't close deals)
Quota (est.)12-20 qualified meetings booked/month

Company Context

Stage: Series A ($61M raised in Nov 2024, $65M total)

Size: ~70 employees

Growth: Actively hiring sales team, fresh capital to deploy

Market Position: Challenger in a rapidly crowding space - competing against Intercom, Ada, Sierra, Decagon, Poly.ai, and dozens of other voice AI/agent platforms. Category is hot but noisy.


GTM Reality

Pipeline Sources:

  • 95% Outbound - you're building lists, cold calling, running email sequences
  • 5% Inbound - occasional demo requests from website, but minimal inbound engine at this stage
  • No PLG motion - this is enterprise software, not self-serve

SDR/AE Structure: You book meetings, hand off to AEs. Standard outbound SDR setup.

Support: Leadership is focused on training and development (per the post), but you're expected to be self-sufficient on prospecting activity.


Competitive Landscape

Main Competitors: Intercom, Ada, Sierra, Decagon, Poly.ai, Leaping AI, plus legacy providers like Five9/Genesys adding AI features

How They Differentiate: Agent Canvas platform with 90%+ resolution accuracy claim, multi-modal support (chat/voice), enterprise governance features

Common Objections:

  • "We're already piloting AI agents with [competitor]"
  • "Our support is too complex for AI to handle"
  • "We just implemented [CCaaS platform] last year"
  • "What's different about you vs. the other 15 AI vendors who called this month?"

Win Themes: Enterprise-grade governance, high resolution rates, handles complex workflows (not just simple FAQ bots)


What You'll Actually Do

Time Breakdown

Cold Calling/Emails (60%) | Research/List Building (20%) | Follow-ups/Nurture (15%) | Internal (5%)

Key Activities

  • Cold Calling: 50-70 dials per day to VP Customer Support, Head of CX, Customer Service Directors. You're trying to get past executive assistants and office managers at mid-market and enterprise companies. Most calls go to voicemail. When you get someone live, you have 20 seconds to pitch why AI voice agents are worth a 30-minute demo.

  • List Building: 1-2 hours/day researching companies with large support teams. You're looking at job postings (are they hiring support agents?), LinkedIn employee counts, press releases about customer growth. Ideal targets: companies with 50+ support agents, high call volumes, growing fast.

  • Email Sequencing: Writing and sending personalized outbound emails (8-12 touchpoints per prospect). You're referencing their tech stack, recent company news, support job postings. Response rates are probably 1-3% if your targeting is good.

  • Demo Qualification: When someone agrees to meet, you're running a 10-15 minute discovery call to confirm they're legit (do they have budget authority? actual pain? timeline?). You need to hand qualified opportunities to AEs, not tire-kickers.


The Honest Reality

What's Hard

  • Cutting through the noise: Every support leader is getting pitched AI solutions constantly. "We're different" is not a compelling hook anymore. You need very tight, specific value props.

  • Gatekeepers: Getting to VP-level buyers means going through EAs, office managers, and "just send me an email" blockers. Direct dials are hard to find for these roles.

  • Long consideration cycles: Even when you book a meeting, deals take 4-6 months to close (for the AE). You won't see immediate impact from your work. Some of your best meetings won't close for quarters.

  • Skepticism about AI: You're selling during peak AI hype, which means buyers are skeptical. They've been burned by AI vendors promising magic and delivering underperforming bots.

What Success Looks Like

  • Booking 12-20 qualified demos per month that convert to opportunities for AEs
  • 50-70+ dials per day with personalized, researched outreach
  • Response rate of 2-4% on email sequences
  • AEs accept 80%+ of your meetings as truly qualified (not tire-kickers)

Who You're Selling To

Primary Buyers:

  • VP Customer Support / Head of Customer Experience (enterprise)
  • Director of Customer Operations (mid-market)
  • Sometimes CCOs or COOs at smaller companies

What They Care About:

  • Reducing cost per contact / cost per resolution
  • Handling volume spikes without hiring more agents
  • Improving CSAT while deflecting simple inquiries
  • Agent burnout and retention issues
  • Speed to implement (they've been burned by 9-month implementations before)
  • Security/compliance for regulated industries

Requirements

  • Thick skin - you'll hear "no" or get hung up on 50+ times per day
  • Discipline to make high call volume even when it feels futile
  • Research skills to find the right targets and personalize outreach
  • Willingness to learn enterprise software sales (complex buying committees, long cycles)
  • Coachable attitude - this is an "invest in you" culture per the post, but that means taking feedback and iterating
  • No prior experience required, but any B2B prospecting experience is helpful