Head of Sales (AI & Automation)
At Alegra, we build more than software: we give superpowers to SMBs, and we want you to be part of it! 💼✨
If you look at a sales funnel and immediately think about what could be automated, redesigned or connected better through AI, this role will probably feel familiar.
We’re not looking for a traditional Head of Sales.
We’re looking for someone who understands commercial systems deeply and knows how to use AI, automation and data to help a revenue organization scale smarter.
At Alegra, you’ll work on the systems behind the commercial operation: workflows, CRM architecture, lead intelligence, automation and funnel optimization across a fast-growing SaaS company in Latin America.
About Alegra 🚀
Alegra is a cloud-based accounting and financial ecosystem helping thousands of SMBs across Latin America operate smarter every day.
We are a team of 500+ people working 100% remotely across 8 countries, building products and systems that simplify how businesses manage sales, invoicing, accounting and operations.
AI is becoming part of how we work across the company, from product development to internal workflows and decision-making. It’s not a side project. It’s part of how we operate.
Your Mission 🚀
Your mission will be to design and scale the systems behind Alegra’s commercial operation.
You’ll help us build a smarter and more scalable revenue organization by connecting AI, automation, CRM architecture, workflows and commercial intelligence into a single operating system.
This is a highly cross-functional role that works closely with Revenue, Product, Growth, Customer and Data teams.
The operational side of sales is already covered by managers and team leaders. Your focus will be improving how the system works behind the scenes.
What You’ll Do
Design and improve the architecture behind our commercial funnel across different customer segments.
Build scalable workflows and automations between CRM stages, lead actions and commercial processes.
Define the logic, triggers and data structure behind the customer journey inside HubSpot.
Improve lead intelligence, pipeline visibility and funnel performance using AI, automation and data.
Analyze commercial conversations and funnel behavior to identify patterns, friction points and optimization opportunities.
Work closely with RevOps, Product, Growth and Customer teams to align systems, processes and revenue initiatives.
Transform commercial insights into actionable inputs for Product and Growth teams.
Help create a commercial operation that is more scalable, measurable and less dependent on manual execution.
Drive visibility around commercial metrics, OKRs and operational performance across the revenue organization.
How You’ll Use AI in This Role
Analyze sales conversations using AI tools to identify patterns, objections and opportunities for improvement.
Build and optimize AI-assisted workflows for outreach, follow-ups and CRM operations.
Improve lead scoring and pipeline prioritization using automation and predictive signals.
Automate reporting, alerts and operational processes that reduce manual work for the commercial team.
Explore and implement new AI tools that improve execution, visibility and scalability across the funnel
What We’re Looking For
Required
5+ years of experience in GTM Systems, Revenue Operations, Commercial Intelligence, Sales Strategy or related roles in SaaS or tech companies.
Strong understanding of commercial funnels, revenue operations and CRM architecture.
Hands-on experience building workflows, automations and scalable operational systems.
Advanced experience with HubSpot, Salesforce or similar CRMs beyond the UI level.
Experience implementing automations in production environments.
Strong business communication skills and ability to work directly with leadership stakeholders.
Experience working cross-functionally with Revenue, Product, Data or Growth teams.
Experience with AI workflows, AI agents or automation tools like Zapier, Make, n8n or similar.
Advanced English proficiency.
Nice to Have
Startup or high-growth SaaS experience.
Founder or builder background.
Engineering background (Industrial, Systems, Software, Mechatronics or similar).
This Role Is a Great Fit If You… ✅
Enjoy building systems more than maintaining manual processes.
Naturally think in workflows, logic and operational scalability.
Like combining business context with technical problem-solving.
Feel comfortable working in fast-changing environments.
Are curious about AI and constantly explore better ways to improve how teams operate.
Prefer ownership and execution over rigid structures.
Think beyond isolated tasks and understand how decisions impact the entire funnel.
This Role Is Probably Not for You If… ⛔
You’re looking for a traditional sales leadership role focused mainly on managing sellers.
You prefer highly structured environments with little change.
You don’t enjoy working with systems, automation or AI tools.
Your experience is mainly operational sales management without exposure to workflows, funnel design or commercial systems.
You prefer execution-only roles without ownership over process design and improvement.
What Our CRO Says About This Role
“If you read ‘sales funnel’ and immediately start thinking about the workflows, automations and missing triggers behind it, that’s exactly the mindset we’re looking for.
We want someone who can help us turn a strong commercial team into a smarter and more scalable operation.”
What You’ll Find at Alegra 💚
AI-First Culture:
Access to AI tools and licenses.
Internal AI innovation initiatives and experimentation spaces.
A team where using AI is part of everyday work.
Remote Work:
100% remote work.
Stable long-term opportunity.
Monthly coworking spaces with local teams.
Professional Growth:
Career development opportunities.
Access to educational platforms and certifications.
Wellbeing:
Wellness initiatives and healthy habits programs.
Additional personal care days during the year.
Benefits & Experience:
Budget to improve your work setup.
Birthday bonus and half-day off.
A multicultural team across different countries.
Diversity at Alegra
At Alegra, we value and promote diversity and inclusion in all forms.
All applications are considered regardless of gender identity, sexual orientation, ethnicity, religion, age, disability or any other characteristic.
If you need accommodations during any stage of the hiring process, please let us know.
Move from homework to AI-powered work. 🤖💚
- Departamento
- Strategy
- Ubicaciones
- Colombia, México , Republica Dominicana, Costa Rica, Argentina
- Estado remoto
- Completamente remoto
- Tipo de empleo
- Tiempo completo