Positive work indicates positive energy transfer from the e.g field to a mass. via the increase of kinetic energy
$\int F \cdot dr$
$\int F \cdot vdt$
$\int m (dv/dt) \cdot vdt$
$m \int d/dt(1/2 v^2)dt$
$1/2 mv^2$
Plugging in bounds from v0 to v1 where shows this is the difference of kinetic energy
so net positive work indicates a positive kinetic energy change, and net negative work equals negative kinetic energy change
The definition
W= -change in U
Means that if there is a positive change in U, then negative work is done
and if there's a negative change in U, positive work is done
There is no contradiction, as U is defined as the amount of work done against the field from A to B, if positive work is done against the field moving something from A to B then the field does negative work on the object moving from A to B meaning a decrease in Work done on the object
As change in U is defined as $\int_{a}^{b} -F \cdot dr $
This represents the work I would have to do against the field moving something from a to b. Taking the minus out,
$\int_{a}^{b} -F \cdot dr =- \int_{a}^{b} F \cdot dr $
The term on the right is - work done by the field so if Potential difference from A to B is positive then F.dr has to be negative, aka negative work done
EDIT:
To conceptualise this,
consider the equation.
$ke + \int_{a}^{x} F \cdot dr = 0$
Where ke is the amount of energy that the object has initially, e.g in the form of kinetic for this example.
This equation states that, given it has some kinetic energy, in moving from a distance (a to x) the field F does work on the object, such that the total kinetic energy when the object has reached a distance x is zero.
Rearranging for ke,
$Ke = - \int_{a}^{x} F \cdot dr $
This is the kinetic energy an object should have, if I want to reach a position x in the presence of a force field such that the object stops at x
This is what potential is defined as ,but instead of saying a particle has some initial ke, the energy could be given over a distance. same thing.
This is WHY this expression represents work done by an external force(me) to move something from a to b against a force field F , clearly if positive work is required to move something from a to b in the presence of forcefield F, then the forcefield F must do negative work on the object moving through that distance ( as I have to give it energy to move it there, because the field does negative work along the way)