Director of Sales Enablement (San Francisco OR Toronto) at PagerDuty
San Francisco, CA, US / Toronto, CA
At PagerDuty, we believe that people do their best in a culture that fosters inclusion, innovation, and success. Our values - Champion the Customer, Take the Lead, Run Together, Ack + Own and Bring Yourself - serve as the foundation of our collaborative and dynamic culture. Whether it’s conducting a retrospective, participating in our monthly Hackdays, cranking out a new product feature, supporting our two PagerDuty bands, or doing our day to day work, Dutonians live and breathe these five values every day. Together, we solve real customer issues and fulfill our mission of connecting teams to real-time opportunities and elevate work to the outcomes that matter.  
Why We Need You
PagerDuty is getting ready for our next phase of growth! We need to ensure our sales force is ready to sell our diversifying products to different levels of buyers across the enterprise and commercial segments. Reporting to the VP of Sales and Business Operations you will be responsible for empowering and leading a dynamic team of Dutonians, arming an effective sales organization at all levels to have the right conversations with buyers at the right time.

How You Contribute to Our Vision

    • Build and develop a team of sales enablement professionals to build a world-class strategy and execution plan that covers all aspects of supporting a fast-growing, SaaS and velocity based sales organization.
    • Hiring the right profiles, core training by role for new product, messaging, and skills based competencies are a few of the key components of a strategy that addresses positive and measurable outcomes.
    • Metrics would also include sales productivity, new-hire ramp time, skills competencies, certifications, etc. in your overall enablement plan. Roles include all customer facing teams including technical and solutions consultants.
    • Act as key partner to sales management by sourcing, developing and delivering programs that improve sales competencies, confidence and high level selling skills.
    • Work collaboratively with product marketing, solutions consultants and other internal teams to develop and deliver highly effective and repeatable sales messaging, selling tools and collateral all within a strategy and process framework.
    • Work cross-functionally across all global organizations to ensure that the sales team is aware of all important company initiatives, communications is streamlined and both administrative and time out of the field is minimized.
    • Build and maintain an enablement delivery platform that provides sales and soon the channel with the content and learning they need in a scalable and measurable way.
    • Integrate and partner with sales operations to ensure seamless GTM on all systems, tools and processes the field uses on a day-to-day basis including enablement on those systems and tools.

About You

    • Strategic, seasoned sales enablement leader with extensive experience developing and delivering enablement program that achieve tangible results. This includes effective sales training, on-boarding programs, sales certifications, sales tools and the best sales events (kick off/bootcamps).
    • A history of building enablement programs aligned to business strategies that make it easy for sales teams to effectively, consistently and efficiently execute.
    • Strong communications, as well as program and project management skills
    • Experience with Sales Manager training and sales coaching
    • Proven track record of creating and delivering impactful sales training and development programs.
    • Excellent motivational and mentoring skills; ability to influence and inspire.
    • Experience working with Sales Operations and with


    • 8+ years sales enablement experience or a combination of sales, sales training and enablement
    • 3-5 years experience in high-velocity, high-growth, high-energy start-up environments, preferably in the SaaS space.
    • BA/BS required.

Heidi Burns

Community Manager

Heidi joined WIN in February 2016 as Head of Community. Prior to WIN, Heidi founded Project Happy Hearts and has held positions at DocuSign, Eventbrite and H.Bloom. She studied business at Cal Poly San Luis Obispo and has her Masters in Social Entrepreneurship from University of Southern California, Marshall School of Business. As a Southern California native she enjoys spending her spare time at the beach and rooting for the Lakers.

Patrick Blute

Community Manager

Patrick Blute is from Cape Cod, Massachusetts. Before studying Sustainable Development at Columbia University, Patrick was a travel show host touring in over 54 countries. He has worked with companies such as Switch Communications, BackOffice Associates, National Geographic, and as a theatre producer in New York. He is an active alumni of the Coca-Cola Scholars Foundation and passionate about content creation, event management, and public speaking. Patrick is extremely excited to work in the intersection of technology and culture.

Jonathan Pines


jp Before joining WIN, Jonathan co-founded GiftRocket (Y Combinator W11) and was a Software Engineer at Facebook. He is also an active angel investor. Jonathan studied math at Stanford and CS at Harvard. He enjoys thinking about interesting ideas and helping founders make them happen.

Kevin Webb


kw Having grown up and been educated in Silicon Valley, Kevin has had little choice but to become completely dependent on the Internet. He studied Human Biology at Stanford, and has worked at companies such as Dash Navigation (acquired by RIM) and FunnyOrDie, as well as the Santa Clara County Public Health Department and the American Museum of Natural History in New York. Kevin’s background lies primarily in writing, web design, and social marketing, and when he’s not working on WIN, he’s generally spending time with friends or writing field shows for the Stanford Band.

Jeremy Schneider


jJeremy Schneider joined WIN as a Senior Associate in January, 2011. Prior to WIN, Jeremy was a Senior Associate Consultant at Bain & Company in San Francisco, where he focused on technology companies and worked in the Private Equity Group. He graduated Summa Cum Laude, Phi Beta Kappa from Dartmouth College, where he majored in History. He has a Master’s degree in Economic and Social History from The University of Oxford, where he was a Clarendon Scholar. Jeremy grew up in the Bay Area and is thrilled to have the opportunity to work closely with entrepreneurs and to immerse himself in the world of start-ups.

Michael Neril

Co-Founder and Affiliate

Michael has worked with technology startups for 15 years as an advisor, investor, co-founder or operator.   Michael is a co-foundmner of Webb Investment Network (“WIN”), which he launched in 2010. As Managing Director, Michael led all investment activities for the firm, focused largely on enterprise cloud applications, marketplaces, and mobile marketing platforms, investing in over 50 companies across these sectors. Prior to WIN, Michael worked at LiveOps, a cloud-based contact center and labor marketplace, where he ran business development for its next-generation virtual work marketplace.  While there, he also incubated and ran the fastest growing product line within the Company. Michael joined LiveOps after it acquired the second of two technology startups which he co-founded called Ooreka, a virtual work marketplace.  Michael started his career as an investment banker in ING Barings’ Technology Group where he primarily advised venture-backed startups on M&A and corporate finance activities. Michael is also a mentor at several startup accelerators. Michael earned a BA in International Relations from Tufts University.  

Maynard Webb


mw Maynard Webb is a 30-year veteran of the technology industry. An active leader in the technology and business community, Maynard serves as a board member, investor, philanthropist and mentor to young entrepreneurs. As the founder of the Webb Investment Network (WIN), a seed investment firm dedicated to nurturing entrepreneurs, Maynard brings his experience developing and leading high-growth companies. WIN provides its portfolio companies with mentorship and on-demand access to an affiliate network of over 80 industry experts.

Irene Webb


“iw” Irene has been involved in the tech world since 1982. After graduating Rutgers with a degree in statistics, and forecasting sales for Breck and Pine Sol products at American Cyanamid, she went on to earn her MBA from East Carolina University. Eager to begin her tech career outside of her home state of New Jersey, she took a programming job (and later finance roles) with IBM in Boca Raton, Florida where she first met Maynard. Irene later worked at Thomas Conrad and then Quantum Corp before taking leave to focus on her family. She came out of retirement in 2010 to manage WIN's finances. When not managing WIN's budget, Irene enjoys traveling and playing golf.

Katie So’Oto

Executive Assistant

“ks” Katie comes to WIN with years of administrative experience from her prior roles at Tellme, (a Microsoft subsidiary), Russell Reynolds Associates and most recently Sofinnova Ventures. She brings a wonderful, positive attitude and service oriented approach to her role. Katie is a bay area native and lives in Redwood City with her husband and four boys.

Dena Porter

Business Operations Manager

WINteamHeadshotsDPDena brings more than a decade of ‘behind-the-scenes’ productivity and organizational knowledge to the fast-flowing stream of information and infrastructure at WIN. She has held positions in Silicon Valley start-ups fusionOne and Baynote and has teamed with Maynard for years at eBay, LiveOps and now WIN. Dena is fascinated by all things technology keeping her in tune with WIN’s existing and prospective portfolio companies.