Andy Woods

Sales Development Representative

DualEntry

SDROutbound HeavyTransactionalRemote📍 Remote
Sales Cycle: 2-4 weeks from first touch to booked demo
Posted by Andy Woods

Overview

You're finding and qualifying finance leaders who need better accounting software. Your targets are CFOs at Series A/B startups, controllers at mid-market companies, and finance ops people at fast-growing e-commerce/SaaS businesses. You're booking first calls for AEs, not running full discovery. Your pitch is simple: they can automate a ton of manual finance work with AI.


Role Snapshot

AspectDetails
Role TypeOutbound SDR with inbound follow-up
Sales MotionOutbound-heavy (60/40)
Deal ComplexityTransactional (booking meetings)
Sales Cycle2-4 weeks from first touch to booked demo
Deal SizeN/A (SDR role)
Quota (est.)15-20 qualified meetings/month

Company Context

Stage: Series A ($90M raised, Khosla/Lightspeed/GV)

Size: 56 employees

Growth: Scaling fast post-funding. GTM team is small but hiring. You're building the outbound motion.

Market Position: Category creator - first AI-native ERP. You're not just competing with other tools, you're convincing people they need a new approach to finance software.


GTM Reality

Pipeline Sources:

  • 40% Inbound - Website demo requests, content downloads, webinar sign-ups. You're following up fast and qualifying whether they're real buyers or students.
  • 60% Outbound - Cold prospecting to companies that raised funding (Crunchbase), Shopify stores scaling fast, Series A/B software companies hiring finance people.

Your Role: You're the first touch. You book the meeting, AE runs discovery and demos. Clean hand-off is critical - bad leads waste everyone's time.

Tools You'll Use: Outreach/SalesLoft for sequencing, ZoomInfo/Apollo for data, LinkedIn Sales Nav, Crunchbase for funding signals.


Competitive Landscape

Main Competitors:

  • Legacy systems: QuickBooks, NetSuite, Sage Intacct
  • Modern alternatives: Various finance ops tools (Ramp, Brex on the expense side)

Your Job: You're not doing competitive positioning (that's the AE's job), but you need to know enough to qualify. If they just signed a 3-year NetSuite contract, they're not a real opportunity.

Common Brush-Offs:

  • "We're happy with QuickBooks" → Dig into team size, transaction volume. Are they actually happy or just not actively looking?
  • "Too busy right now" → Finance people are always busy. That's the problem you solve.
  • "Send me some info" → Classic blow-off. You need to create urgency.

What You'll Actually Do

Time Breakdown

Outbound Prospecting (50%) | Inbound Follow-up (25%) | Meetings/Admin (25%)

Key Activities

  • List Building: You're identifying target accounts. Companies that raised Series A/B in the last 6 months. Fast-growing Shopify stores (check BuiltWith). Software companies with 20-100 employees hiring a controller. You're building lists in Apollo/ZoomInfo and researching their current setup.

  • Cold Outreach: 40-60 LinkedIn messages per day to CFOs, controllers, and finance ops people. Personalized opening line (congrats on the funding round, saw you're hiring a controller), then straight into the pain point: "Most companies your size have 3-4 people in finance. Our customers run similar operations with 1-2. Worth a 15-minute call?" Email sequences running in parallel.

  • Inbound Follow-up: Demo requests come in from the website. You're calling within 5 minutes. Some are legit (CFO at a Series B company), some are noise (students, consultants). You're qualifying: company size, current tools, who makes the decision, timeline.

  • Objection Handling: Lots of "too busy," "not looking right now," "we just implemented [other tool]." You're not trying to overcome every objection - you're finding people with active pain. If they're happy with their setup, move on.

  • Meeting Coordination: Once you get interest, you're booking time on the AE's calendar, sending pre-meeting context (company size, current setup, pain points), and confirming attendance the day before.


The Honest Reality

What's Hard

  • Finance people don't respond like sales/marketing people: Lower reply rates on cold outreach. CFOs are slammed. You need more touches to get a response. Expect 1-2% reply rates on good days.

  • Category creation is a grind: You can't just say "we're better than NetSuite" - you're explaining why they need a new approach. That's a longer, more educational conversation. Harder to create urgency.

  • Limited brand awareness: You're not selling Salesforce. Most people haven't heard of DualEntry. You're earning trust from scratch every time.

  • Qualification is tricky: Finance software buying process is complex. The person who responds isn't always the decision-maker. You need to find the CFO, but they're the hardest to reach.

  • Early-stage chaos: Messaging will change. ICP will shift as you learn. What works this month might not work next month. Less structure than a mature SDR org.

What Success Looks Like

  • Booking 15-20 qualified meetings per month (qualified = right title, company fits ICP, active pain)
  • AEs accepting 80%+ of your meetings (good qualification, not wasting their time)
  • 30-40% of your meetings leading to demos/next steps (shows you're finding real interest)
  • Finding repeatable outbound motions (which signals work, which messages get replies)

Who You're Selling To

Primary Targets:

  • CFOs at Series A/B startups (20-100 employees)
  • Controllers at mid-market companies ($10M-100M revenue)
  • Finance/Ops leaders at high-growth e-commerce or SaaS companies

What They Care About:

  • Pain points you're listening for: Hiring more finance people, manual work (reconciliations, revenue rec), scaling issues, outgrowing QuickBooks
  • Buying signals: Just raised funding, recently hired a CFO/controller, complaining about finance ops on LinkedIn
  • Timing: Finance software changes happen during fiscal year planning or after audit pain. Q4/Q1 is busy season.

Requirements

  • 0-2 years in SDR/BDR role (or looking to break into SaaS sales)
  • Comfortable with high-volume outreach (this isn't an inbound-only role)
  • Strong written communication - your LinkedIn messages and emails need to be tight
  • Resilience - finance people are hard to reach, rejection is constant
  • Curiosity about the product - you need to understand enough to qualify pain
  • Willingness to figure it out - early-stage company means less established playbook