Paolo Lipari

Sales Development Representative (SDR)

OutboundHub

SDROutbound HeavyTransactional
Posted by Paolo Lipari•

Overview

You're an SDR working for an agency that sells outbound services to Italian B2B software companies. Your day is spent prospecting on behalf of 1-3 client companies at once—cold calling, emailing, and LinkedIn outreach to book meetings for their sales teams. You report to Paolo (the founder) and work remotely.


Role Snapshot

AspectDetails
Role TypeAgency SDR (multi-client)
Sales Motion100% outbound (cold calling, email sequences, LinkedIn)
Deal ComplexityN/A - you're booking meetings, not closing deals
Sales CycleN/A - measured on meetings booked
Deal SizeN/A
Quota (est.)15-25 qualified meetings/month across all clients

Company Context

Stage: Bootstrapped / Early-stage

Size: 6 employees

Growth: Founded to serve Italian B2B SaaS market (€5-20M ARR companies)

Market Position: One of several SDR agencies competing for Italian mid-market software companies


GTM Reality

Your Work Environment:

  • You're not prospecting for OutboundHub—you're the product
  • You work on 1-3 client accounts at once, each with different ICP, messaging, and product
  • Clients are Italian B2B software companies trying to book meetings with their target accounts
  • You get lists, sequences, and messaging frameworks from client success/ops team

Support Structure:

  • Small team means you're likely collaborating directly with founder on strategy
  • No layers of management—feedback is immediate and direct
  • You'll probably help with reporting, CRM hygiene, and client updates beyond just prospecting

Competitive Landscape

Main Competitors: Other SDR agencies (Martal Group, SalesRoads, dozens of smaller EU-focused shops)

How They Differentiate: Focus on Italian market, enterprise experience, fast ramp time

Common Objections: "We tried an SDR agency before and it didn't work", "We can hire cheaper in-house", "Your team won't understand our product"

Win Themes: Results in 2-4 weeks, predictable costs, no hiring/managing overhead


What You'll Actually Do

Time Breakdown

Calling (50%) | Email/LinkedIn (30%) | Admin/Client Reporting (20%)

Key Activities

  • Cold Calling: 60-80 dials per day across multiple client campaigns. Most go to voicemail. You're trying to get 2-3 conversations per hour that could lead to a meeting. Calling in Italian to Italian prospects.
  • Email Sequences: Writing and sending personalized emails (often 50-100/day). You're A/B testing subject lines, tweaking messaging, following up on cold calls. Open rates are 20-30%, reply rates are 2-5%.
  • LinkedIn Outreach: Connection requests and follow-up messages. This is lower volume but sometimes higher conversion than cold email. You're managing multiple client LinkedIn accounts or using your own profile.
  • Meeting Qualification: When someone responds positively, you're asking discovery questions to confirm they fit the client's ICP before booking them on the AE's calendar. Some people agree to meet but aren't actually qualified.
  • CRM Updates: Logging every call, email, and outcome in the client's CRM (likely HubSpot or Salesforce). This takes more time than you'd think.
  • Client Reporting: Weekly or bi-weekly syncs with each client showing activity metrics and meeting quality. You need to explain why some weeks are slower than others.

The Honest Reality

What's Hard

  • Context Switching: You're switching between 2-3 different products/ICPs throughout the day. Hard to get into a flow when you're selling HR software one hour and cybersecurity the next.
  • Rejection Volume: You're getting rejected all day, every day. Most calls don't connect. Most emails don't get replies. You need thick skin.
  • Quality vs Quantity Tension: Clients want volume but also complain if meeting quality is low. You're constantly balancing speed with personalization.
  • Client Blame: When meetings don't convert to pipeline, clients sometimes blame your qualification. You don't control what happens after the handoff.
  • Language Barrier: If you're not a native Italian speaker, you're at a disadvantage. Nuance matters in cold calls.
  • Small Team = Lots of Hats: You'll probably do stuff beyond pure prospecting—help train new SDRs, build out sequences, update client decks.

What Success Looks Like

  • Consistently booking 15-25 qualified meetings per month (5-8 per client if you have 3 clients)
  • High show rates (70%+ of booked meetings actually happen)
  • Clients renew their contracts with OutboundHub, which depends partly on your meeting quality
  • You learn multiple outbound motions and can talk intelligently about different industries

Who You're Calling (Varies by Client)

Typical Buyer Profiles for Italian B2B Software:

  • Sales Directors / VPs at mid-market companies (50-500 employees)
  • Head of Operations / COO at growing companies
  • IT Directors / CTOs (if client sells technical product)

What They Care About:

  • "Is this actually relevant to my business or are you spraying?" (They get spammed constantly)
  • "Can you prove ROI quickly?" (Budget scrutiny in current economy)
  • "Do you understand the Italian market?" (They're tired of generic US-style sales pitches)

Requirements

  • Fluent Italian (native or near-native)—you're calling Italian companies
  • English proficiency for internal team communication
  • 6-12 months SDR experience or strong hunger to learn outbound (they might hire raw talent)
  • Comfortable with rejection and high-volume prospecting
  • Self-motivated for remote work (no one's watching you make calls)
  • Basic CRM skills (HubSpot/Salesforce)
  • Willingness to work on multiple client accounts simultaneously