How does electoral work support or undermine grassroots organizing efforts?

The new website OrganizingUpgrade.com runs a monthly "Fast Forum" column with the hope of drawing out new ideas and encouraging new voices to take a stab at the freshest challenges facing our community. This month, we asked four organizers for their reflections on the question:
How does electoral work support or undermine grassroots organizing efforts?
Here is the response by Oakland Rising's Field Director, Jessamyn Sabbag:
Over the last 8 months I have run two electoral field campaigns and a civic engagement program that has collectively impacted over 14,000 Oakland residents. As Field Director for Oakland Rising, I spend a lot of time thinking about the possible marriages between electoral and grassroots organizing. It’s not an easy concept. 500 words is too short. But below I will examine three “marriages” that I have been trying to address in my work. And I’ll show how Oakland Rising is intentionally working to develop integrated grassroots and electoral organizing to build the power we need to win, to move the issues and advance the agendas of low-income communities of color to the center of city government.
1)    Culture Shifting: From Struggle to Winning
2)    Quantity AND Quality: One Hand Washes the Other
3)    Developing Leaders: Cross-Over Skills and Issues
 
1)  Culture Shifting: From Struggle to Winning
Since coming to Oakland Rising as Field Director, I’ve learned a bunch of quotes to describe our tactics and strategy.  One of my favorites is “We don’t believe in struggle.  We believe in winning.”  Oakland Rising is on the path towards developing a collaborative model that harnesses the scale we need for electoral power and the depth we need for grassroots progressive social change.   But shifting the grassroots base and intermediary organizations from a model and history of struggle to a model and program based on winning at all costs takes time.  We all agree theoretically that electoral organizing is different from grassroots organizing, including the realities of a short lead time for electoral planning, and a fast paced environment to achieve goals of significant scale.  Over the last 9 months, I have had the opportunity to usher in culture shifts by developing models that integrate the science of electoral organizing with the equation to build grassroots power.
2) Quantity AND Quality
Oakland Rising is committed to developing the quantity we need to win at the ballot box and the quality of voters we need to hold elected officials accountable. In our latest campaign, our scale nearly doubled when we contacted over 12,000 Oakland voters about local campaigns like the development of a local transit hub. In our 2-4 minute electoral style conversations we were able to engage in political education and get community feedback (outside of the social justice “base”) that helps redirect grassroots campaign framing and increase follow-up.  And our base-building organizations are currently doing more in-depth outreach with voters who were IDed as “hot contacts.”
3) Developing Leaders
Few things are more satisfying than a good win, right?  Fortunately, electoral organizing offers a couple opportunities a year to get a good win (especially here in California where it seems like we have an election every other month!). While phoners and canvassers can do quick-hit issue education and identify the supporters we need to win on election day, moving that win into a community of leaders takes strategic grassroots organizing.  Oakland Rising hires organizational volunteer leaders and community members to phone and knock as members of the electoral daily team.  Volunteer leaders who work on our Daily Team developed or deepened a new skill set which is continually used to help with grassroots organization-specific campaigns.