Outbound SDR

Overview

You're prospecting into finance departments at mid-market and enterprise companies to book demos for Tipalti's AP automation platform. You spend most of your day cold calling CFOs, Controllers, VPs of Finance, and AP managers who already get pitched by BILL, Coupa, AvidXchange, and others. Your job is to get 15-20 minutes on their calendar for an AE to walk through the product.

Role Snapshot

Company Context

Stage: Series D+ (last known valuation $8.3B, raised $150M in 2023)

Size: 1,193 employees

Growth: Expanding into Canada (just launched localized Canadian solution in Dec 2024), actively hiring after promoting 2 SDRs to AE

Market Position: Established player in a crowded AP automation space—competing against BILL, Coupa, AvidXchange, Brex, Stampli, and others. Not the scrappy underdog, not the category creator. They're in the fight.

GTM Reality

Pipeline Sources:

• 20% Inbound - marketing-generated leads (webinars, content downloads, demo requests), quality varies
• 80% Outbound - your cold calls, emails, LinkedIn outreach to targeted account lists
• Some partner/referral flow but not a primary channel

SDR/AE Structure: Dedicated SDRs feed dedicated AEs. You're booking meetings for specific reps. When you hit quota, you can get promoted (both reps on your future manager's team just got promoted to AE, so there's a path).

SE Support: AEs have access to Sales Engineers for technical demos, but you won't work with them much as an SDR.

Competitive Landscape

Main Competitors: BILL AP/AR, Coupa, AvidXchange, Brex, Stampli, Airbase

How They Differentiate: Tipalti positions as more comprehensive (AP + mass payments + procurement + expenses in one platform), better for global/multi-entity companies, stronger for high-volume payouts

Common Objections: "We already use BILL/Coupa," "Our ERP handles this," "We're not ready to change systems," "Too expensive for our size"

Win Themes: Global capabilities, integration depth with ERPs, compliance/security for regulated industries, handles complex multi-entity scenarios

What You'll Actually Do

Time Breakdown

Cold Calling (50%) | Email/LinkedIn (25%) | Research/List Building (15%) | Internal Meetings (10%)

Key Activities

• Cold Calling: 60-80 dials per day to CFOs, Controllers, VPs of Finance, AP Directors. Most don't answer. Gatekeepers are common. You're leaving voicemails and trying to get past assistants.
• Email Sequences: Running multi-touch cadences (7-10 touches over 2-3 weeks). Personalization at scale—researching pain points, recent news, tech stack signals before hitting send.
• LinkedIn Outreach: Connection requests and InMails to finance leaders. Lower response rate than you'd hope. Most ignore you.
• List Building: Using tools like ZoomInfo, LinkedIn Sales Nav, 6sense to identify target accounts and contacts. Segmenting by company size, industry, tech stack (looking for companies on NetSuite, Sage Intacct, etc.).
• Meeting Qualification: When someone bites, you're asking discovery questions to confirm budget authority, pain points, timeline. Passing junk meetings to AEs gets you coached quickly.
• Internal Syncs: Daily stand-ups, weekly 1:1s with your manager, pipeline reviews, training sessions on messaging/objection handling.

The Honest Reality

What's Hard

• High Rejection Volume: You're interrupting busy finance people who weren't looking for a solution. Most calls go to voicemail. Most emails get ignored. You need thick skin.
• Crowded Category: Every mid-market company already has AP automation on their radar or is using a competitor. You're not educating a new market—you're trying to displace incumbents or catch buying cycles.
• Qualification Pressure: Not every meeting counts. If you book someone with no budget, wrong title, or no timeline, it doesn't hit quota. AEs will kick it back and you get no credit.
• Repetitive Grind: Same calls, same objections, same pitch hundreds of times per week. The job is volume-based.

What Success Looks Like

• Hit 15-20 qualified meetings/month consistently: Get into a rhythm where you're booking 3-5 meetings per week that AEs accept and show up for
• 25%+ connect rate on calls: Getting better at timing (early mornings, late afternoons), using local presence numbers, crafting voicemails that get callbacks
• Promotion within 12-18 months: If you hit quota and show sales acumen, you can move to AE (like the two reps who just got promoted on this team)

Who You're Selling To

Primary Buyers:

• CFOs (at smaller mid-market companies, 100-500 employees)
• VPs of Finance / Controllers (at larger mid-market and enterprise, 500-2000 employees)
• AP Directors / AP Managers (influencers, sometimes economic buyers at enterprise)

What They Care About:

• Time savings: How many hours per week does this save their AP team?
• Error reduction: Duplicate payments, fraud risk, compliance gaps
• Visibility/control: Real-time spend visibility, approval workflows, audit trails
• Integration: Does it play nicely with their ERP (NetSuite, Sage Intacct, Dynamics, Oracle)?
• Global capabilities: Multi-currency, international vendor payments, tax compliance
• ROI: Can you show payback period under 12 months?

Requirements

• 1-2 years of SDR/BDR experience (or proven ability to handle high-volume cold calling)
• Comfortable with rejection—you'll hear "no" or get ignored 90%+ of the time
• Coachable and metric-driven—you need to track your activity and iterate on what works
• Some understanding of B2B finance/accounting helpful (knowing what AP, GL, ERP mean)
• Ability to work in Toronto office (this isn't a remote role based on the posting context)