Two bullet points should never describe the same exact thing, but they are encouraged to support and contextualize one another.
The bullets should flow, chronologically if possible, and the images they portray must collaborate to construct a detailed, step-by-step narrative of your time spent in a given job or experience.
Think of each cluster of lines under a job title as responsible for collaborating on a chapter of your career. The list of bullets should answer this line of questioning clearly:
How did your actions build upon one another over the time you spent in a given position? Where did you start in the role, where did you end up, and how did you get there?
A collection of several lines can work together to assemble a compelling story:
Worked closely with Founder/CEO on key business development in state-wide education.
Recruited 4 sales reps & account managers in Q2 to scale outreach & ongoing contracts.
Closed first 15 institutional contracts averaging 3k per district in Q1 2014.
Designed and implemented our inside-sales strategy to 40,000 school systems.
When reading through these lines you can visualize what happened: you started focusing on statewide education. You recruited people to help you. Then you closed your first 20 deals. From there, you built a sales strategy to expand to the world.
Make your lines march the story down the page. There is a sense of continuity at play. Read a line, enhance the picture, and repeat.