Alessio Uyema Nakatahara

Account Executive - Chile

UiPath

Account ExecutiveOutbound HeavyEnterprise📍 Chile
Deal Size: $80K-300K+ ACV
Sales Cycle: 4-9 months
Posted by Alessio Uyema Nakatahara•

Overview

You're selling UiPath's robotic process automation (RPA) and AI platform to enterprise companies in Chile. You'll be cold calling and emailing IT directors, operations leaders, and digital transformation teams at banks, insurance companies, manufacturers, and large service organizations to book discovery calls and demos. Most of your time goes into prospecting, running technical discovery calls, and coordinating proof-of-concepts with technical stakeholders.


Role Snapshot

AspectDetails
Role TypeFull-cycle AE (likely self-sourcing heavy)
Sales MotionOutbound-heavy with some inbound from marketing
Deal ComplexityEnterprise - technical, multi-stakeholder
Sales Cycle4-9 months
Deal Size$80K-300K+ ACV (enterprise RPA deals)
Quota (est.)$800K-1.2M/year

Company Context

Stage: Public (NYSE: PATH)

Size: 5,096 employees

Growth: Established player but dealing with market headwinds—RPA adoption has slowed as AI-native tools emerge. They're pivoting messaging to "agentic automation" to stay relevant.

Market Position: Category creator and leader in RPA, but facing increased competition from Microsoft Power Automate, Automation Anywhere, and new AI workflow tools.


GTM Reality

Pipeline Sources:

  • 30% Inbound - marketing generates some leads from digital transformation content, webinars, analyst reports. Quality varies—lots of tire kickers and students wanting to learn RPA.
  • 60% Outbound - you're doing cold outreach to target accounts. Expect a lot of phone tag with IT departments and LinkedIn messages that go unanswered.
  • 10% Partners - some referrals from consulting firms (Deloitte, Accenture) who implement UiPath, but these are competitive and slow-moving.

SDR/AE Structure: Likely self-sourcing in Chile market—SDR teams are typically focused on major markets (US, UK). You might get some marketing leads, but you'll be doing most of your own prospecting.

SE Support: Shared Solutions Engineer pool, likely based in Brazil or regional hub. You'll need to coordinate time zones for technical demos and POCs.


Competitive Landscape

Main Competitors: Microsoft Power Automate (bundled with Office 365), Automation Anywhere, Blue Prism, and increasingly AI-native tools like n8n or enterprise workflow platforms.

How They Differentiate: UiPath has the most mature platform with strongest orchestration and AI capabilities. They emphasize their "agentic automation" vision and platform breadth vs point solutions.

Common Objections:

  • "We already have Power Automate included in our Microsoft license"
  • "RPA is just screen scraping—we need real AI"
  • "We tried RPA before and the bots kept breaking"
  • Price—UiPath is premium vs alternatives

Win Themes: Platform maturity, enterprise governance, AI + RPA integration, strong partner ecosystem for implementation.


What You'll Actually Do

Time Breakdown

Prospecting (45%) | Active Deals (35%) | Internal/Admin (20%)

Key Activities

  • Cold outreach: You're making 30-40 calls/day and sending 50+ emails/week to IT directors, COOs, and heads of digital transformation. Most don't respond. You're trying to get 8-10 first meetings per month.
  • Discovery & demo calls: When you get a meeting, you're running discovery to understand their manual processes, then doing a platform demo. These are technical—expect questions about API integrations, security, and how bots handle exceptions.
  • Managing POCs: Deals require proof-of-concept where the prospect tests UiPath on 1-2 processes. You're coordinating with your SE, the customer's IT team, and business users. POCs take 4-8 weeks and many stall or get deprioritized.
  • Multi-threading: You're dealing with 4-6 stakeholders per deal—business sponsor, IT security, procurement, operations team that will use the bots. Lots of internal politics and competing priorities. You're constantly chasing people for the next meeting.
  • Proposal & negotiation: Enterprise procurement cycles are slow. Legal reviews, security assessments, budget approvals. Deals slip quarters regularly.

The Honest Reality

What's Hard

  • Long, unpredictable cycles: Deals take 6-9 months on average. You'll have a pipeline that looks healthy but closes at 15-20% because of budget freezes, internal project delays, or customers choosing cheaper alternatives.
  • Education burden: You're often introducing RPA to companies that don't fully understand it. Lots of calls explaining the difference between RPA, workflow automation, and AI. This gets repetitive.
  • Technical complexity: Prospects have detailed questions about architecture, scaling, bot maintenance, and integration with their legacy systems. You need your SE for most technical conversations.
  • Microsoft competition: Power Automate is bundled with Office 365, so you're constantly justifying the premium price. Deals often come down to "good enough" vs "best in class."
  • Territory building: Chile is likely greenfield territory, so you're starting from scratch—no established pipeline, no account history, no warm intros.

What Success Looks Like

  • Closing 3-5 new enterprise deals per year at $100K+ ACV each
  • Building a pipeline of 15-20 active opportunities worth $3-5M total
  • Getting 1-2 expansion deals from existing Chilean customers (if any exist)

Who You're Selling To

Primary Buyers:

  • CIO / Head of IT (ultimate budget owner)
  • VP of Operations / COO (business sponsor)
  • Head of Digital Transformation (champion)
  • IT Director / Automation Lead (technical evaluator)

What They Care About:

  • ROI proof: They want to see clear cost savings from automating manual processes. You'll be calculating FTE (full-time equivalent) savings.
  • Implementation risk: Previous automation projects may have failed. They're worried about bots breaking, maintenance burden, and change management.
  • Scalability: Can they start with 5 bots and grow to 50? How does governance work at scale?
  • Security & compliance: Especially in banking/insurance—detailed questions about data handling, access controls, audit trails.

Requirements

  • 3-5 years enterprise software sales experience, preferably in Chile or LATAM markets
  • Fluent in Spanish and English (you'll report to regional leadership, likely in English)
  • Experience selling technical/infrastructure software—need to grasp RPA concepts and speak credibly to IT buyers
  • Comfortable with long sales cycles and complex, multi-stakeholder deals
  • Self-starter who can build territory from scratch without a lot of hand-holding
  • Willingness to travel within Chile for customer meetings (banks won't always take Zoom calls for enterprise deals)