Lecture from Manny Medina, CEO of Outreach: Insights on Sales Strategies and Growth

Overview

• Manny Medina, CEO and co-founder of Outreach
• Attempting to read every significant sales book
• Contrasting old school vs. new school sales approaches
• The evolution of sales techniques and the importance of closing strategies
• Outreach's journey from inception to over $200 million ARR

Sales Literature Journey

• Numerous new sales books released frequently
• Common themes and recurring titles in sales literature
• Comparison of old school (e.g., Zig Ziggler, Brian Tracy) vs. new school sales
• Old school: Emphasis on always be closing (ABCs)
• New school: More steps, emphasis on challenging the customer, passive-aggressive tones
• Personal experiences of customers rarely volunteering orders
• The societal shift in sales techniques mirroring broader social changes

Introduction of Manny Medina

• CEO and co-founder of Outreach
• Company has over 200 million ARR, 1,000 employees, 6,000 customers
• Focus on outbound sales strategies and company evolution

Outreach's Journey

Initial Steps and Pivot

• Started as a company in the recruiting space, pivoted towards sales engagement software
• Created an engine for personalized, scalable email outreach
• Transitioned to a SaaS company for appointment setting
• Identified larger market in sales teams vs. recruiting teams

Outbound Sales Strategy

• Absolute necessity for outbound due to creating a new product category
• Educating the market was essential: no existing demand
• Product-market fit and founder-led sales were critical
• Outbound sales as foundational to company growth
• Enterprise customers lacked budgets initially; had to generate need and budget

Company's Growth Phases

0 to 10 Million ARR

• Diverse customer base: selling to anyone who would buy
• Realized the need to narrow the Ideal Customer Profile (ICP)

10 to 100 Million ARR

• High-velocity, smaller deals transitioned to larger, strategic deals
• Sales cycles became longer but resulted in stickier, more strategic deals
• Emphasis on professional services and change management

100 Million+ ARR

• Multi-product strategy
• Expansion through selling additional products to existing customers
• Shift from new logo acquisition to expansion of existing accounts

Internationalization Strategy

• First international market: EMEA
• Began with support and customer success, then expanded sales
• Lesson learned: Importance of a definitive strategy and focusing on market segments

Competitive Landscape

• Competition can be beneficial for market establishment
• Using strength in the existing market to capture additional areas
• Differentiating by focusing on creating and improving workflows

Marketing and Category Establishment

• Marketing efforts coinciding with category establishment
• Impact on conversion rates and market awareness
• Importance of brand and event marketing efforts

Outbound vs. Inbound

• Outbound is necessary for new categories and immediate growth
• Inbound marketing took longer to become a significant growth driver
• The interplay of outbound efforts with marketing to increase effectiveness

Final Advice and Reflections

• Challenges at different growth stages (10, 25, 50, 100 million ARR)
• Transitioning sales approach from features, to solutions, to the value created
• Understanding growth milestones not as endpoints but as continuous journeys
• Importance of creating a repeatable and scalable sales system

Conclusion

• Continue building upon successful strategies
• Continuous learning and adaptation in sales strategies
• Outbound sales remains a crucial part of growing SaaS companies