Director of Sales Operations – RFP/Proposal Management, Enterprise Software

San Diego, CA | Direct Hire

Post Date: 11/22/17 Job ID: 17110202 - P Industry or Function: Software Compensation: $100,000 to $125,000

JOB #: 17110202 - P

JOB DESCRIPTION: Thriving, Pre-IPO “Social Good” Technology Company is hiring a new Director of Sales Operations and RFP’s / Proposals. They have significant VC Funding and several multi-million dollar contracts in place with commercial and government customers. Typical sales cycles are several months long, with complex processes involving 200+ page RFPs to win multi-year deals in the $1-10M range. This is an ideal role for someone who has experience working with major Fortune 100 and/or government customers with complicated sales processes that require top level strategy as well as attention to detail.

Their differentiated SaaS product suite is designed to address challenges facing governments and large corporations, including security, accessibility, cost, and sustainability. As Director of Sales Operations, you will report to the VP of Sales and manage a small team of bid managers and proposal/RFP writers. You’ll also work closely with multiple internal teams and earn their respect to get their collaboration on proposals. Strategically, you will review potential customers and pipeline to determine viability of deals.

This is a fit for a strong Sales Leader who loves challenges, can herd cats, and wants to make a difference to the bottom line of a growing company and, at the same time, better the world!

To apply, send your resume for confidential review to Kanani Masterson ( This is a fulltime position based in San Diego, CA. Please read qualifications carefully and only apply if you meet key criteria.

Job Duties:
Manage small team working on proposal/RFP process from strategy through publishing
Hire and manage current and future Sales Operations staff including Technical Writers
Oversee aspects of CRM management (Salesforce) and reporting including activity and pipeline reporting
Work with Marketing to implement campaigns and sales collateral
Data analysis of market trends, sales performance, and strategic targets
Ensure that digital tools and style guides are in place to support the development of digital documentation that meet current market expectations
Review proposal pricing, get CFO sign off, ensure pricing is positioned for success
Review legal sections of contracts with legal team
Be an advisor to other Directors; Focus on sales enablement, reporting and analytics, and strategy and planning
Be a strong advocate to ensure customer requirements are implemented as promised and delivered on time to top quality standards
Provide recommendations and take actions based on strategic objectives, forecast, or performance metrics
Enhance sales productivity by enabling the team to work smarter by simplifying processes, evaluating new tools/apps, and providing easy access to information and resources needed to close sales

Salary Range and Bonus Potential:

$100,000 to $125,000 (bonuses starting at 25% of base)
• Performance bonuses / commissions

• Comprehensive health benefits (medical, dental, vision)
• Casual and supportive environment.
• 401K

Job Requirements:
Must have 10+ years' experience in Sales Operations or related function, preferably in enterprise software sales environment, government sales, healthcare, or other complex, long-runway sales environment.
Must have worked in position managing teams selling multimillion dollar products or services. Ideally enterprise software
A minimum of seven (7) years of successful management experience over teams creating complex proposals and RFPs.
Demonstrable knowledge of writing and editing documents with specified formats, with the inclusion of appropriate text, tables, charts, graphics, indexes, and appendices.
Successful track record of working with sales and technical / operational resources to develop and write content
Talented and proactive “Cat Herder”: Track record in driving change and removing hurdles in fast growth organizations by working cross-functionally with Product, Operations, and Engineering
Experience working in startups or emerging organizations preferred. Understanding of how to manage up and down, and build and grow a successful and sustainable team.
Exceptional people and communication skills; Ability to explain the problems at hand, and more importantly, how to solve them; ability to solve problems creatively.
Current, hands-on expertise with all phases of the sales cycle along with a deep understanding of sales management issues.
Working knowledge of Google Drive, MS Office and Project, and graphics packages.

Educational Requirements:
• Bachelor's degree or master’s degree in Business, English, or related field from accredited college or university or equivalent experience, is preferred.


KEYWORDS: director of sales, sales operations, proposals, proposal manager, rfp, government, healthcare, insurance, SaaS, PaaS, software, Sales Director, Writer, sales manager, proposal director, director of business development, enterprise software sales, enterprise sales business development

Kanani Masterson

I joined the TriStaff Group in January 1999 as a Technical Recruiter, and am now Director of Recruiting for our Technology, Marketing, and Executive Search Division. My regional focus is the Greater San Diego Area and Southern California. I work with large public companies as well as funded, fast-growth startups, and am passionate about keeping up with whatever disruptive new advances are happening in the technology space. To date, I've placed over 940 candidates, and produced over $8.5M in placement fees, and most importantly I love helping people and companies thrive and grow... I'm lucky to love what I do! Areas of Specialty: SaaS, enterprise software, security, machine learning, robotics, online advertising, social media, mobile apps, telecommunications, cloud computing, medical devices, consumer electronics, big data/analytics, clean tech; Positions: Software Engineers, Web Developers, Firmware Engineers, Solutions Architects, Network/Systems Engineers, Systems Engineers, Systems Administrators, Product Managers, C-Level positions (COO, CMO, CTO, CFO, CIO, CRO, CEO, etc.), Supply Chain, Operations, Quality Assurance, Marketing, Business Development & Sales, and Finance. I'm a native San Diegan (I grew up in Solana Beach, CA) and attended La Jolla Country Day School from 6th grade through high school graduation. I attended the University of Southern California (USC) as a Dean’s Scholar and Golden State Scholar, and graduated BA Degree in Creative Writing & Poetry. I also have one spunky young daughter and a fantastic husband.
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