Dennis Osterloh - Co-Founder & CEO

Q: Where is Dennis based?

Dennis is based in Paphos, Cyprus .

Q: What languages does Dennis speak?

Dennis speaks the following languages: German (Native), English (Advanced), Spanish (Elementary) .

Q: How many years of experience does Dennis have?

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 4 months . Note that Dennis may not have shared all experience and actually has more experience.

Q: What is Dennis's latest experience?

Dennis's most recent position is Co-Founder & CEO at Connect AI .

Q: What companies has Dennis worked for in recent years?

In recent years, Dennis has worked for Connect AI , Stay Digital AI , Instaffo GmbH , and Emetriq GmbH / Telekom AG .

Q: Which industries is Dennis most experienced in?

Dennis is most experienced in industries like Advertising , Telecommunication , and Information Technology (IT) . Dennis also has some experience in Professional Services , Tourism and Hospitality , and Real Estate .

Q: Which business areas is Dennis most experienced in?

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 (IT) .

Q: Which industries has Dennis worked in recently?

Dennis has recently worked in industries like Advertising , Telecommunication , and Information Technology (IT) .

Q: Which business areas has Dennis worked in recently?

Dennis has recently worked in business areas like Product Development , Marketing , and Project Management .

Recommended expert

Paphos, Cyprus

Experience

Jan 2024 - Present

2 years 2 months

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.

Jan 2022 - Dec 2024

3 years

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.

Jan 2022 - Dec 2022

1 year

Mannheim, Germany

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.

Jan 2017 - Dec 2022

6 years

Hamburg, Germany

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).

Aug 2014 - Jun 2017

2 years 11 months

Bremen, Germany

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.

Industries Experience

See where this freelancer has spent most of their professional time. Longer bars indicate deeper hands-on experience, while shorter ones reflect targeted or project-based work.

Experienced in Advertising (6 years), Telecommunication (6 years), Information Technology (4 years), Professional Services (3 years), Tourism (3 years), and Real Estate (2 years).

Advertising

Telecommunication

Information Technology

Professional Services

Tourism

Real Estate

Business Areas Experience

The graph below provides a cumulative view of the freelancer's experience across multiple business areas, calculated from completed and active engagements. It highlights the areas where the freelancer has most frequently contributed to planning, execution, and delivery of business outcomes.

Experienced in Product Development (10.5 years), Marketing (8.5 years), Sales (7 years), Project Management (6 years), Business Intelligence (3 years), and Information Technology (3 years).

Product Development

Marketing

Sales

Project Management

Business Intelligence

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

German

Native

English

Advanced

Spanish

Elementary

Profile

Created

November 2025

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Frequently asked questions

Do you have questions? Here you can find further information.

Where is Dennis based?

Dennis is based in Paphos, Cyprus.

What languages does Dennis speak?

Dennis speaks the following languages: German (Native), English (Advanced), Spanish (Elementary).

How many years of experience does Dennis have?

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 4 months. Note that Dennis may not have shared all experience and actually has more experience.

What roles would Dennis be best suited for?

Based on recent experience, Dennis would be well-suited for roles such as: Co-Founder & CEO, Head of Product, Head of Audience Insights.

What is Dennis's latest experience?

Dennis's most recent position is Co-Founder & CEO at Connect AI.

What companies has Dennis worked for in recent years?

In recent years, Dennis has worked for Connect AI, Stay Digital AI, Instaffo GmbH, and Emetriq GmbH / Telekom AG.

Which industries is Dennis most experienced in?

Dennis is most experienced in industries like Advertising, Telecommunication, and Information Technology (IT). Dennis also has some experience in Professional Services, Tourism and Hospitality, and Real Estate.

Which business areas is Dennis most experienced in?

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 (IT).

Which industries has Dennis worked in recently?

Dennis has recently worked in industries like Advertising, Telecommunication, and Information Technology (IT).

Which business areas has Dennis worked in recently?

Dennis has recently worked in business areas like Product Development, Marketing, and Project Management.

What is the availability of Dennis?

Dennis is immediately available for suitable projects.

What is the rate of Dennis?

Dennis's rate depends on the specific project requirements. Please use the Meet button on the profile to schedule a meeting and discuss the details.