Dennis Osterloh-Co-Founder & CEO
Check rate
Experience
Co-Founder & CEO
Connect AI
Founded and built an AI-agent SaaS for automated customer support and lead qualification, including implementation at pilot customers.
Structured and led a remote team in engineering, LLM ops, and customer enablement.
Developed and launched AI agents for website inbound, lead qualification, and customer service with 8K€ MRR.
Mohr Immobilien – Reduced response time from >24h to <5 minutes, increased viewing requests by 20–35%, and reduced lead loss.
PTC E-Commerce – Automated product data & support workflows, ~10–15h/week less effort per support employee.
Co-Founder & CEO
Stay Digital AI
Built and led an automation agency for trade and SMEs with a focus on scalable process and sales automation.
Developed and implemented robust automation architectures in sales, service & back office.
Grew from 0 to 8 employees and €1M revenue within 14 months.
Delivered 50+ digital and process automation projects, measurable in time savings & throughput increase.
Grüne Leuchte GmbH – Sales: ~30% revenue increase & ~10–25h/month time savings through an automated funnel.
DRS Holding – Recruiting: increased applications from 3/month to 35/month using a WhatsApp application chatbot.
Head of Product
Instaffo GmbH
Repositioned the company internally to a recruiting platform.
Built cross-functional teams, prioritization systems, and product-centered growth mechanics.
Developed the product vision and translated it into a clear platform and go-to-market strategy.
Evolved cross-functional teams (product, engineering, design) into autonomous units.
Introduced user-centered product development and validation processes (Discovery → Delivery).
Responsible for team & product on web & mobile, including roadmap, prioritization & release management.
Head of Audience Insights
Emetriq GmbH / Telekom AG
Responsible for product strategy, revenue growth, and leading a team for an AI-based audience insights platform in the enterprise segment.
Led a cross-functional team of ~20+ people (product, UX, engineering, data, design).
Designed an organizational structure with hierarchy and sociocracy approach so teams could take ownership without losing speed or clarity.
Developed a clear product vision and translated it into a scalable platform strategy.
Built a sales & marketing funnel.
Introduced agile product management structures (Scrum/Kanban), including roadmap and prioritization processes.
Redeveloped & launched Audience Insights with enterprise deal sizes >€100k based on value-based pricing.
Achieved >30% revenue growth on the existing product (add tech targeting) through platform sales (e.g., via Google).
Product Lead
Traum-Ferienwohnungen GmbH
Enhanced the travel platform focusing on growth, user retention, and actively shaping the shift from hierarchy to self-organization.
Progressed from working student to product owner and finally to product lead.
Led the highest-revenue business unit (50+ people, including UX, business, marketing, sales, engineering & support).
Helped steer the transition from hierarchical structures to autonomous, cross-functional teams.
Introduced and scaled agile product organization (Scrum/Kanban), including roles & prioritization models.
Built an innovation team to explore and validate new platform features.
Delivered >30% annual revenue growth by optimizing pricing, funnel logic, and customer journeys.
Achieved >100% user retention through host success programs & self-service optimizations.
Reduced costs by 20–50% in marketing, sales & support through process digitization.
Industry experience
See where this freelancer has spent most of their professional time.
Experienced in Advertising, Telecommunication, Information Technology, Professional Services, Tourism, and Real Estate.
Business area experience
See which departments and functions this freelancer has contributed to most.
Experienced in Product Development, Marketing, Sales, Project Management, Business Intelligence, and Information Technology.
Summary
Experience building teams, platforms, and growth systems from early stage to renewal phase.
Built a LinkedIn personal brand as a strategic channel for employer branding, talent acquisition, and lead generation.
Skills
Leadership & Organization:
- Team Building And Leadership
- Agile Organizational Development
- Self-Organization & Hierarchy
- Role & Responsibility Architecture
- Change Management
- Employer Branding
Product & Technology:
- Product Strategy
- Platform Economy
- Customer Journey Design
- Continuous Discovery
- Lean Startup
- Ai-Powered Automation
- No-Code System Architecture
Go-To-Market & Business Impact:
- Value-Based Pricing
- Funnel Optimization
- Revenue & Retention Strategies
- Operational Scaling
- Product Led Growth
- Personal Branding & Content Creation
Own Company Framework - Value
- Visualize: Document Value Creation (Processes, Bottlenecks, Dependencies).
- Align: Structure Roles, Responsibilities, And Workflows.
- Link: Connect Systems & Tools And Implement Initial Process Automation.
- Upgrade: Integrate Data Management & Ai Agents Intelligently For Scaling.
- Evolve: Partially Autonomous Organization With Tech & Data Ownership Strategy.
Languages
Statistics
Experience
Global experience
Expertise
Profile
Frequently asked questions
Have questions? Find more information here.
Dennis is based in Paphos, Cyprus.
Dennis speaks the following languages: German (Native), English (Advanced), Spanish (Elementary).
Dennis has at least 12 years of experience. During this time, Dennis has worked in at least 4 different roles and for 5 different companies. The average length of individual experience is 2 years and 5 months. Note that Dennis may not have shared all experience and actually has more experience.
Based on recent experience, Dennis would be well-suited for roles such as: Co-Founder & CEO, Head of Product, Head of Audience Insights.
Dennis's most recent position is Co-Founder & CEO at Connect AI.
In recent years, Dennis has worked for Connect AI, Stay Digital AI, Instaffo GmbH, and Emetriq GmbH / Telekom AG.
Dennis is most experienced in industries like Advertising, Telecommunication, and Information Technology. Dennis also has some experience in Professional Services, Tourism, and Real Estate.
Dennis is most experienced in business areas like Product Development, Marketing, and Sales. Dennis also has some experience in Project Management, Business Intelligence, and Information Technology.
Dennis has recently worked in industries like Advertising, Telecommunication, and Information Technology.
Dennis has recently worked in business areas like Product Development, Marketing, and Project Management.
The availability of Dennis needs to be confirmed.
Daily rate distribution
The rates shown represent the typical market range for freelancers in this position based on recent contracts on our platform.
Average rates for similar positions
Rates are based on recent contracts and do not include FRATCH margin.
The average daily rate is the mean of all daily rates from recent contracts of comparable freelancers on our platform.
The median daily rate is the middle value of all daily rates — half of comparable freelancers charge less, half charge more. Unlike the average, it is barely affected by outliers.
Calculated based on our freelancers’ daily rates as of 25 Aug 2026. Actual rates may vary depending on seniority level, experience, skill specialization, project complexity, and engagement length.
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