Roberto “Roby” Peñacastro leads a conversational commerce platform built around how customers buy today: via messaging. In this interview-style profile, we trace his path from Google to a scalable B2B SaaS company.
The company now serves 2,800+ clients across 20+ countries and runs with a 70+ person LATAM team. It earned a spot in Forbes Mexico’s 30 Business Promises of 2024, a clear nod to traction and trust.
Expect candid stories about a purpose-driven pivot, a missed-sale that changed course, and the choices that shaped growth. We also explore product plans like native chat, funding moves, and concrete growth metrics.
Beyond one startup, the bigger idea is an ecosystem: a talent launchpad to seed the next wave of founders. Read on for practical, experience-based insights on speed, consistency, and building lasting relationships.
Key Takeaways
- Messaging-first products match how modern customers buy.
- Proof points matter: client count, geographic reach, and team size build credibility.
- Founders learn fastest from missed opportunities and fast iteration.
- Regional talent ecosystems can power a new generation of startups.
- Focus on execution: speed, consistency, and relationships drive scale.
From Slush to Startup: Finding Purpose and Building Momentum
A student exchange in Finland became the pivot point that redirected a trade-focused career toward tech. That moment compressed years of doubt into a clear choice: build products, not just move goods.
The moment that changed everything: Finland, Slush, and Daniel Ek’s wake-up call
At Slush in 2017, a talk by Daniel Ek felt like a wake-up call. It showed how founders shape markets and create fast opportunities. The scene pushed a rethink away from a logistics path toward building a startup.
Early career stepping stones: mienvío, logistics learnings, and the leap to Google
An internship at mienvío put theory into practice. Working in logistics SaaS taught quick problem solving and shipped-first mentality. Later, work at Google with small businesses revealed common growth blockers: slow lead handling and weak follow-up.
“Start messy, learn fast”: the mindset behind speed of execution and consistency
The lesson across these chapters is compounding skill over years. Be a generalist: know enough marketing, sales, finance, and HR to unblock the team. Start imperfectly, iterate quickly, and keep showing up—those insights shaped the product focus on simplicity and fast onboarding.
| Phase | Key Learning | Impact on Product |
|---|---|---|
| Slush / Finland | Founder mindset, network opportunities | Priority on speed and market fit |
| mienvío (logistics) | Operational problem solving | Workflow-first design |
| Understanding small businesses | Simple onboarding, rapid follow-up tools |
What Leadsales Does and Why Conversational Commerce Is Winning in Latin America
One missed WhatsApp reply once cost the team $25,000 and clarified the mission: response time, not demand, was the true bottleneck for many SMBs.
What it is: This platform centralizes conversations and converts messages into trackable sales workflows. Instead of scattered inbox chaos, teams get a single pipeline view where chat is native and deals move through stages.
- Lifecycle coverage: Discovery → Consideration → Purchase → Post-Purchase → Re-Engagement → Awareness.
- Omnichannel reach: WhatsApp, Instagram, Messenger, SMS, Email, Telegram, X, TikTok and more—managed with context intact.
- Speed-to-value: Plug & play onboarding under five minutes for non-technical users.
Conversational commerce works in Latin America because customers naturally buy inside chat. Small and medium businesses run sales inside social DMs and messaging apps. When volume grows, response time breaks and revenue slips away.
Positioning vs. legacy CRMs: Unlike email-first solutions such as HubSpot, Salesforce, or Pipedrive, this tool treats instant chat as the core sales motion. That makes it a better fit for companies aiming to turn conversations into recurring revenue and stronger customer relationships.
| Metric | Snapshot | Why it matters |
|---|---|---|
| Clients | 2,800+ companies | Proof of product-market fit across the region |
| Reach | 20+ countries | Regional scale in Latin America |
| Team | 70+ LATAM staff | Local talent for local problems |
Ecosystem impact: The long-term goal is to build a talent-dense pipeline—what the team calls a “mafia” of alumni founders—so the industry benefits multiply beyond a single company.
Roberto Peñacastro – Co-founder & CEO – Leadsales on Growth, Funding, and Scaling a High-Performance Team
Early traction and clear metrics turned a fast-moving idea into a fundraising story. The company was built by bootstrapping first: real customers and real recurring revenue mattered more than slide decks. TechCrunch later noted the team reached 1,400+ customers and ~$1.6M ARR before pursuing venture capital.
Bootstrapping milestones and why customers beat polish
Before seed funding, traction looked like steady customer growth and repeatable revenue. That proof made conversations with investors practical and focused.
Berkeley SkyDeck as a turning point
In September 2021 the team entered SkyDeck with ~300 customers. The accelerator invested $200k for 7.5% equity. Workshops, advisor matching, and demo pressure helped scale from ~300 to nearly 900 customers and to roughly $1M in annual recurring revenue during the program.
Seed round, expansion, and what the capital is for
After SkyDeck, a $3.7M seed led by Ulu Ventures and Blue Pointe Ventures closed. That capital is earmarked for hiring and market expansion — notably Brazil, where WhatsApp-led commerce is huge and native payments are emerging.
Leadership and the mastermind advantage
Operating principles are simple: move fast, be a generalist, build strong relationships, and keep intensity sustainable. The founder credits Think and Grow Rich for the “mastermind” idea—surrounding yourself with people who multiply execution and resilience.
| Phase | Metric | Impact |
|---|---|---|
| Bootstrapped | 1,400+ customers, ~$1.6M ARR | Proof before pitch |
| SkyDeck | $200k for 7.5%; ~300→900 customers; ~$1M ARR | Network and investor access |
| Seed | $3.7M led by Ulu & Blue Pointe | Hiring & Brazil expansion |
Conclusion
A single turning point and a lost $25,000 sale crystallized a simple mission: make chat count for revenue. This tidy line captures the journey from a purpose pivot to a platform built for measurable sales and steady growth.
The company proved traction with 2,800+ clients across 20+ countries and a 70+ LATAM team. Early wins, SkyDeck momentum, and seed funding turned fast execution into repeatable expansion for the business.
What stands out: native chat at the center of workflows, omnichannel coverage, and lifecycle-focused tools that let teams convert conversations into revenue. Those solutions cut response time and keep the customer context intact.
For operators: tighten response time, centralize conversations, measure the funnel, and build a mastermind-level network. Conversational commerce in latin america is a practical playbook now influencing global tech and business trends.
Want deeper insights? Visit the Leadsales site or follow public channels to track the journey and practical lessons for your team.
FAQ
Who is Roberto Peñacastro and what is his role at Leadsales?
What inspired the shift from early career roles to founding a startup?
How did experience at mienvío and in logistics influence product design?
What core mindset does he promote for startup execution?
How did a missed WhatsApp message highlight market opportunity?
How big is Leadsales today and which markets does it serve?
What capabilities does the Leadsales platform offer?
Which messaging channels does Leadsales support?
How quickly can a business get started with Leadsales?
How does Leadsales differentiate from HubSpot, Salesforce, and Pipedrive?
What is the broader ecosystem vision behind Leadsales?
How did bootstrapping and venture funding shape the company’s growth?
What was the significance of joining Berkeley SkyDeck?
What metrics signaled product-market fit and growth milestones?
FAQ
Who is Roberto Peñacastro and what is his role at Leadsales?
Roberto Peñacastro is the co-founder and CEO of Leadsales. He leads strategy, product direction, and growth initiatives while building partnerships across Latin America to help SMBs improve sales via conversational commerce tools and automation.
What inspired the shift from early career roles to founding a startup?
A defining moment came during a visit to Slush in Finland where a conversation about product-market fit and urgency sparked the decision to pursue startups full-time. Past roles in logistics and at Google provided operational lessons and exposure to product thinking that made the leap practical.
How did experience at mienvío and in logistics influence product design?
Working in logistics taught practical customer workflows, handling returns, and the importance of timely communication. Those learnings shaped Leadsales’ focus on speed, simple integrations, and messaging-first pipelines tailored for SMB needs.
What core mindset does he promote for startup execution?
He advocates a “start messy, learn fast” approach—prioritize speed of execution, iterate quickly, and maintain consistency. This mindset helps teams validate ideas, reduce time-to-market, and build durable habits that scale.
How did a missed WhatsApp message highlight market opportunity?
A lost sale worth about ,000 due to a missed WhatsApp lead revealed how many SMBs lack reliable conversational workflows. That gap showed there was a large addressable market for tools that centralize messaging and automate follow-up.
How big is Leadsales today and which markets does it serve?
Leadsales serves 2,800+ clients across more than 20 countries with a team of 70+ professionals in LATAM. The platform targets small and medium businesses seeking to modernize sales using conversational channels.
What capabilities does the Leadsales platform offer?
The platform manages the full customer lifecycle—from discovery and qualification to sales and re-engagement—using native chat, omnichannel messaging, pipeline views, automation, and analytics designed for rapid onboarding.
Which messaging channels does Leadsales support?
Leadsales is omnichannel by design and integrates WhatsApp, Instagram, Messenger, SMS, Email, Telegram, and other popular messaging tools so teams can centralize conversations and keep context across platforms.
How quickly can a business get started with Leadsales?
The product is built for speed with plug & play onboarding. SMBs can connect messaging channels, import contacts, and see a pipeline view with native chat integration in days, enabling immediate revenue impact.
How does Leadsales differentiate from HubSpot, Salesforce, and Pipedrive?
Leadsales focuses on conversational commerce and messaging-first workflows tailored to SMBs in LATAM. It emphasizes fast onboarding, local payments, and channel-specific automations versus broader CRM feature sets that require heavier customization.
What is the broader ecosystem vision behind Leadsales?
The company aims to create a supportive regional ecosystem—a “Leadsales Mafia”—to accelerate founder networks, share talent, and increase startup resilience across Latin America, boosting pipeline and market access for new ventures.
How did bootstrapping and venture funding shape the company’s growth?
Early bootstrapped traction proved product-market fit, which made the company an attractive candidate for VC. Initial capital allowed faster hiring, product expansion, and regional growth while preserving the culture of resourcefulness.
What was the significance of joining Berkeley SkyDeck?
Berkeley SkyDeck provided a catalytic 0k investment for 7.5% equity, and access to Silicon Valley mentors, investor introductions, and validation that accelerated the company’s go-to-market strategy and fundraising momentum.
What metrics signaled product-market fit and growth milestones?
Growth from 300 to nearly 900 customers and reaching roughly
FAQ
Who is Roberto Peñacastro and what is his role at Leadsales?
Roberto Peñacastro is the co-founder and CEO of Leadsales. He leads strategy, product direction, and growth initiatives while building partnerships across Latin America to help SMBs improve sales via conversational commerce tools and automation.
What inspired the shift from early career roles to founding a startup?
A defining moment came during a visit to Slush in Finland where a conversation about product-market fit and urgency sparked the decision to pursue startups full-time. Past roles in logistics and at Google provided operational lessons and exposure to product thinking that made the leap practical.
How did experience at mienvío and in logistics influence product design?
Working in logistics taught practical customer workflows, handling returns, and the importance of timely communication. Those learnings shaped Leadsales’ focus on speed, simple integrations, and messaging-first pipelines tailored for SMB needs.
What core mindset does he promote for startup execution?
He advocates a “start messy, learn fast” approach—prioritize speed of execution, iterate quickly, and maintain consistency. This mindset helps teams validate ideas, reduce time-to-market, and build durable habits that scale.
How did a missed WhatsApp message highlight market opportunity?
A lost sale worth about $25,000 due to a missed WhatsApp lead revealed how many SMBs lack reliable conversational workflows. That gap showed there was a large addressable market for tools that centralize messaging and automate follow-up.
How big is Leadsales today and which markets does it serve?
Leadsales serves 2,800+ clients across more than 20 countries with a team of 70+ professionals in LATAM. The platform targets small and medium businesses seeking to modernize sales using conversational channels.
What capabilities does the Leadsales platform offer?
The platform manages the full customer lifecycle—from discovery and qualification to sales and re-engagement—using native chat, omnichannel messaging, pipeline views, automation, and analytics designed for rapid onboarding.
Which messaging channels does Leadsales support?
Leadsales is omnichannel by design and integrates WhatsApp, Instagram, Messenger, SMS, Email, Telegram, and other popular messaging tools so teams can centralize conversations and keep context across platforms.
How quickly can a business get started with Leadsales?
The product is built for speed with plug & play onboarding. SMBs can connect messaging channels, import contacts, and see a pipeline view with native chat integration in days, enabling immediate revenue impact.
How does Leadsales differentiate from HubSpot, Salesforce, and Pipedrive?
Leadsales focuses on conversational commerce and messaging-first workflows tailored to SMBs in LATAM. It emphasizes fast onboarding, local payments, and channel-specific automations versus broader CRM feature sets that require heavier customization.
What is the broader ecosystem vision behind Leadsales?
The company aims to create a supportive regional ecosystem—a “Leadsales Mafia”—to accelerate founder networks, share talent, and increase startup resilience across Latin America, boosting pipeline and market access for new ventures.
How did bootstrapping and venture funding shape the company’s growth?
Early bootstrapped traction proved product-market fit, which made the company an attractive candidate for VC. Initial capital allowed faster hiring, product expansion, and regional growth while preserving the culture of resourcefulness.
What was the significance of joining Berkeley SkyDeck?
Berkeley SkyDeck provided a catalytic $200k investment for 7.5% equity, and access to Silicon Valley mentors, investor introductions, and validation that accelerated the company’s go-to-market strategy and fundraising momentum.
What metrics signaled product-market fit and growth milestones?
Growth from 300 to nearly 900 customers and reaching roughly $1M in annual recurring revenue were key indicators of product-market fit, demonstrating repeatable sales motion and strong customer retention.
What are the next steps after seed funding?
Seed capital has funded expansion plans—especially into Brazil—strengthened the product roadmap, and enabled hires in sales, engineering, and customer success to scale ARR and deepen market penetration.
What leadership principles guide team building and sustainability?
Key principles include being a generalist leader who connects dots across functions, investing in relationships, and creating sustainable work rhythms that balance hustle with long-term wellbeing.
Which book influenced his leadership and strategy?
Think and Grow Rich influenced his approach by highlighting the value of the “mastermind” concept—collective thinking, accountability, and shared ambition as a growth multiplier for leaders and teams.
M in annual recurring revenue were key indicators of product-market fit, demonstrating repeatable sales motion and strong customer retention.
What are the next steps after seed funding?
Seed capital has funded expansion plans—especially into Brazil—strengthened the product roadmap, and enabled hires in sales, engineering, and customer success to scale ARR and deepen market penetration.
What leadership principles guide team building and sustainability?
Key principles include being a generalist leader who connects dots across functions, investing in relationships, and creating sustainable work rhythms that balance hustle with long-term wellbeing.
Which book influenced his leadership and strategy?
Think and Grow Rich influenced his approach by highlighting the value of the “mastermind” concept—collective thinking, accountability, and shared ambition as a growth multiplier for leaders and teams.