Sam Gifford

Sales Consultant (Sales Engineer)

Rillet

Sales EngineerBalancedConsultativeRemote📍 NYC, SF, or Remote
Deal Size: $30K-150K ACV
Sales Cycle: 2-4 months
Posted by Sam Gifford

Overview

You're the technical expert who helps AEs close deals by running product demonstrations, answering technical questions, and guiding prospects through evaluations of Rillet's AI-native ERP. Your audience is Controllers, accounting managers, and IT teams who need to understand how Rillet handles their specific GL, AP/AR, and reporting requirements. You translate between accounting workflows and product capabilities.


Role Snapshot

AspectDetails
Role TypePre-sales Sales Engineer
Sales MotionSupporting both inbound and outbound deals
Deal ComplexityConsultative to Enterprise
Sales Cycle2-4 months (you're involved mid-to-late stage)
Deal Size$30K-150K ACV (supporting AE deals)
Quota (est.)Tied to team pipeline or deals influenced (varies by comp structure)

Company Context

Stage: Growth stage (140 employees, scaling GTM team aggressively)

Size: 140 employees total, GTM team grew from 6 to 30 in 6 months

Growth: High momentum - landing public companies and marquee AI startups. Multiple complex implementations happening simultaneously.

Market Position: Category challenger - need to prove technical credibility against established ERPs while evangelizing "AI-native" approach


GTM Reality

How You Work with AEs:

  • AEs own the relationship and commercial conversations
  • You get pulled in after initial discovery when prospects want to see the product or have technical questions
  • You support multiple AEs simultaneously (likely 3-5 AEs per SC given team scaling)

Demo Types:

  • Initial product demos (60 mins) - high-level walkthrough of platform
  • Deep-dive sessions (90-120 mins) - specific workflows like revenue recognition, multi-entity consolidation, custom reporting
  • Technical evaluations - answering integration questions, security reviews, data migration planning

Customization Needs: Some custom demo scenarios based on prospect's industry or current accounting setup, but mostly standard demo environment


Competitive Landscape

Main Competitors: NetSuite, Sage Intacct, QuickBooks Enterprise, traditional ERPs

Technical Differentiation: AI-powered automation (auto-categorization, reconciliation), modern API architecture vs legacy systems, faster implementation than NetSuite

Common Technical Objections:

  • "Can it handle our multi-entity structure?"
  • "How do you integrate with our banking/payroll/Salesforce?"
  • "What's the migration process from NetSuite?"
  • "Where does the AI make decisions and can we audit it?"
  • "Do you have SOC 2?"

What You Need to Prove: That an AI-native system can be trusted with their financial data, that implementation won't be a nightmare, that it won't break their audit trail


What You'll Actually Do

Time Breakdown

Demos & Calls (50%) | Demo Prep & Research (20%) | Internal Alignment (15%) | Product Learning (15%)

Key Activities

  • Running product demos: Walk finance teams through Rillet's platform - GL automation, AP/AR workflows, bank reconciliation, reporting builder. You need to understand their current process ("How do you close your books today?") and show how Rillet streamlines it. Most demos are screen-share, some on-site for enterprise deals.
  • Answering technical questions: Field questions about integrations ("How does data flow from Stripe?"), data migration ("How long to import 5 years of history?"), security ("Where is data stored?"), compliance ("Can we maintain GAAP audit trail?"). Some you answer live, some require follow-up with engineering.
  • Building custom demo scenarios: Before big demos, you prep specific use cases - their chart of accounts structure, their revenue recognition requirements, their multi-entity consolidation needs. This means researching their business and configuring demo data.
  • Supporting technical evaluations: During evaluation phase, you coordinate security questionnaires, provide API documentation, walk IT teams through integration architecture, sometimes build proof-of-concept integrations for complex deals.
  • Internal collaboration: Weekly sync with AEs on pipeline, feedback sessions with product team on feature gaps that lost deals, writing technical content for sales enablement, onboarding new AEs on product capabilities.

The Honest Reality

What's Hard

  • You're supporting a rapidly growing AE team (grew 5x in 6 months), so you're constantly context-switching between deals and may get pulled into demos with little prep time.
  • Finance teams ask incredibly detailed questions about edge cases and compliance scenarios. You need to know when to say "let me confirm with engineering" vs trying to answer something you're not sure about.
  • The product is evolving quickly - new AI features, new integrations, new modules. You're constantly learning what shipped this week and what's on the roadmap vs what doesn't exist yet.
  • Deals stall or die for non-technical reasons (budget cuts, champion leaves, decide not to switch) even when the technical evaluation went great. That's frustrating but part of the job.
  • You'll field some questions that the product can't handle yet - revenue recognition edge cases, specific industry requirements, integrations that aren't built. You need to be honest about gaps while keeping deals alive.

What Success Looks Like

  • Maintaining a high win rate on deals where you're actively involved (demos don't lose to technical objections)
  • AEs want you on their deals because you make them more likely to close
  • Building reusable demo scenarios and technical content that scales the team
  • Prospects trust your technical guidance and see you as a credible expert on finance systems

Who You're Selling To

Primary Audiences:

  • Controllers and accounting managers (hands-on users who will live in the system daily)
  • CFOs and VPs of Finance (care about strategic value and implementation risk)
  • IT/Technical teams at larger companies (security, integrations, data architecture)
  • Sometimes external auditors (need to bless the audit trail and controls)

What They Care About:

  • Can it handle their specific accounting workflows (revenue recognition rules, intercompany eliminations, etc.)?
  • Integration reliability - will data sync correctly from their banking, billing, payroll systems?
  • Implementation timeline and effort - how long to go live, how much data migration work?
  • System security and compliance (SOC 2, data residency, access controls)
  • Reporting flexibility - can they build the custom reports their board/investors need?

Requirements

  • 2-4+ years as an SE/SC, preferably selling fintech, accounting software, or ERP systems
  • Strong understanding of accounting fundamentals (GL, AP/AR, reconciliation, close process) - you don't need to be a CPA but must speak the language
  • Ability to run compelling product demos and think on your feet during technical Q&A
  • Experience with API/integration concepts - can explain how data flows between systems
  • Comfortable learning complex software quickly and explaining it simply to non-technical finance users
  • Low ego - you support AEs, they own the relationship and get credit for the close