Steven Ortmann, CHA
Founding Partner- Head of Enterprise GTM & Partnerships @ Cignara (YC P26)
About
Building Agentic AI. Enterprise AI leader. Award-winning operator. Recovering hotelier. Founding Partner at Cignara (YC 26). We are building The AI Concierge for Enterprise support alongside one of the sharpest founders I've encountered. Also, the CEO & Founder of Gratitude AI LLC, my advisory firm at the intersection of AI and enterprise. 22+ years operating at the highest level. CHA. GM of the Year. 30 Under 30. 40 Under 40. I've led teams, driven culture, and delivered commercial results and now I bring that operator credibility to the AI companies expanding into enterprise, and to the organizations that need someone who's actually run the business to lead their AI transformation. Over the last several months I've had the privilege of working alongside some incredible YC founders and that experience only sharpened my instincts for where AI is actually going and who's building it right. If your enterprise is exploring AI for customer support, or if you're an AI company that needs someone who can open doors and close deals with operators who trust them let's talk. Powered by coffee and gratitude. 12 handicap but my friends think it should be a 10.
United States
San Francisco Bay Area
Hospitality
AI Strategy, Management Consulting, Consulting, Digital Strategy, Strategic Partnerships, Culinary Management, Luxury Travel, Advisory Boards, Board of Directors, Director level, Construction, International Sales, Artificial Intelligence (AI), Business Growth Strategies, Go-to-Market Strategy, Multi-Property Management, P&L Accountability, luxury guest, Capital Expenditures, Revenue Forecasting
Experience

Founding Partner- Head of Enterprise GTM & Partnerships
San Francisco, CA
Excited to join as Founding member of Cignara, a YC-backed enterprise AI company building voice and chat agents that resolve customer support issues end-to-end, not just deflect them. (We also do several other cool things) Leading enterprise sales, partnerships, marketing, operations and creative across all verticals. Already working with Fortune 500 companies bringing 20+ years of operator experience and a network built over a career to help Cignara land, expand and dominate the enterprise customer support market Working directly alongside founder Nalin Gupta to build the company from the ground up.

Founder & Chief AI Officer
Los Angeles, CA
AI leadership for hospitality. Hospitality expertise for AI. As Founder and Chief AI Officer of Gratitude AI Advisory, I serve hotels, ownership groups, management companies, and AI companies entering the hospitality vertical as a Chief Fractional AI Officer. After 22 years in hospitality — standing at the front desk, managing the P&L, leading teams, and serving guests — I watched hotel leadership become buried in vendor pitches, ownership calls, reporting cycles, and compliance reviews. The guest moved to the bottom of the priority list. I spent the last year doing what most AI vendors skip. I learned the tools. Tested the technology. Built the relationships. And combined it with 22 years of knowing exactly what a hotelier's day actually looks like. We sit on your side of the table. Not the vendor's. The result is not a report. It is operational change. Implement. Automate. Get back to providing hospitality.

Chairperson & Co-Founder
Conejo Valley
As Co-Founder and Chairman of the Board for Visit Conejo, I helped establish and grow the official tourism organization for the Conejo Valley region. I played a leading role in the strategic development of Conejo.com, a dynamic platform designed to showcase the region’s unique blend of outdoor recreation, culinary experiences, arts, and overall hospitality. During my leadership, we focused on elevating regional visibility through digital campaigns, hotel partnerships, and community-driven initiatives that positioned the Conejo Valley as a distinct destination nestled between Los Angeles and Santa Barbara. Key initiatives: Launched Conejo.com to highlight hiking trails, restaurants, wineries, events, and lodging in Thousand Oaks, Agoura Hills, Westlake Village, and Newbury Park. Championed hotelier collaboration to drive overnight stays and economic impact. Led brand strategy, marketing, and stakeholder engagement efforts to increase tourism awareness. Promoted the region’s lifestyle appeal through storytelling, influencer outreach, and curated local experiences. My tenure helped lay the foundation for a sustainable and collaborative tourism ecosystem focused on local pride and visitor engagement.

Chief Operating Officer
As Chief Operating Officer, I provided executive leadership across our commercial hospitality portfolio, including The Palm Hotel & Spa and Selvin’s Restaurant & Lounge. My focus spans operations, growth strategy, financial oversight, and creative brand execution. Directly overseeing the operations of all the Department Heads including Operations, Guest Services, Housekeeping, Sales & Marketing, Maintenance and Engineering, Banquets, Restaurant and all F&B related experiences, Accounting and the well-being of 185 plus employees. As a Co-Founder of Selvin’s Restaurant & Lounge, I directed concept development, project management, brand identity including menu creation, and interior design from inception to successful launch. The venue has become an elevated experience catering not only to the hotel guest, but also to the community as a standout dining option. At the portfolio level, I oversee commercial strategy, asset optimization, and performance growth. I lead all business disciplines, operations, sales, culinary, and guest services ensuring alignment with our vision of elevated hospitality and long-term profitability. Additionally, I maintain a strong presence in the community: • Founder & Past Chairman, Conejo Valley Tourism Improvement District • Board Member, California Lutheran University Hospitality Advisory Committee • Chamber Leadership, with current and past board participation across multiple regional organizations My position was eliminated due to liquidation of assets. I remain a minority shareholder of the Palm Hotel & Spa, Inc with no operating obligation.

General Manager
When I assumed leadership at The Palm Hotel & Spa, the property suffered from prolonged mismanagement and operational decline. I took charge of a full-scale repositioning which included rebuilding the hotel’s infrastructure, culture, and service standards from the ground up. Under my guidance, we completed multiple brand identity conversions and implemented a comprehensive operational overhaul. I developed a team-first culture grounded in service excellence, which now drives guest satisfaction and long-term loyalty. Proud moment for the team, we took the hotel from number 9 (last place in the market) and became the #1 Rated Hotel on TripAdvisor for our market. Since taking that title 8 years ago, we have not looked back. Extremely grateful and passionate about what we do every day. Key initiatives include: • Operational turnaround and reorganization • Managing a team of Directors with a focus on “ownership” • Revenue and sales strategy leadership • Guest experiences transformation focused on elevated, memorable service • Strategic renovation planning and implementation • Ongoing brand and identity development to position The Palm as a market leader My role as GM was hands-on, focused on refining the guest journey, maximizing operational efficiency, and identifying new growth opportunities through community partnerships and property enhancements.

General Manager
Thousand Oaks, California, United States
Sales Strategy Consultant – International & Domestic Markets Worked alongside the executive leadership team at Luxe Hotels to strengthen global brand presence and drive targeted sales efforts across the international leisure, corporate, and group travel segments. My role focused on identifying and cultivating high-value relationships with global travel partners, tour operators, and luxury travel advisors to position Luxe (The Palm Hotel) as a premier destination for international travelers. I collaborated cross-functionally with the corporate team and on-property sales leadership to align initiatives and ensure consistent messaging, tailored offers, and market-specific promotions. Key Contributions: Participated in sales missions, trade shows, and travel consortium events to increase visibility and conversion. Advised executive teams on positioning, rate strategy, and distribution channels to optimize bookings. This role deepened my expertise in international hotel sales strategy and cross-market collaboration, while reinforcing my ability to align brand values with culturally relevant outreach for the benefit of our sales team on property.

Crisis Response- Wildfires
California, United States
Supported wildfire crisis response initiatives for Visit California, aligning safety messaging, stakeholder coordination, and tourism recovery efforts to protect communities, restore traveler confidence, and support local economies statewide.

General Manager/Task Force/Operations
San Luis Obispo, California, United States
Employed by Ocean Park Hotels- Provided task force management and on-site operational leadership across a diverse hotel portfolio. Stepped in to stabilize assets, implement brand standards, and train property teams to improve performance. Delivered hands-on hotel management services during transitions, PIP execution, and staffing gaps ensuring continuity, guest satisfaction, and profitability across multiple branded and independent properties. Received the highest SALT scores for operations department.

Board Member
Camarillo, California, United States
Tourism Marketing District that allows local lodging businesses to promote tourism in an effort to increase overnight stays. Funded by a self-assessment, CHTA- (Camarillo Hotel & Tourism Association) is comprised of community leaders passionate about promoting and enhancing the lodging industry and Camarillo community.
Steven Ortmann, CHA's Contact Information
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