Let $V$ be a real $d$-dimensional vector space, and let $1 \le k \le d-1$ be a fixed integer. Let $A,B \in \text{Hom}(V,V)$, and suppose that $AW=BW$ for every $k$-dimensional subspace $W \le V$. Is it true that $A=\lambda B$ for some $\lambda \in \mathbb R$? If not, can we characterize all such pairs $A,B$?
Here are some partial results (proofs at the end):
First, the answer is clearly positive for $k=1$.
Lemma 1: If at least one of $A$ and $B$ is invertible, then the answer is positive.
Lemma 2: We always have $\text{Image}(A)=\text{Image}(B)$. In particular, $\text{rank}(A)=\text{rank}(B)=r$.
Lemma 3: If $r \ge k$ or $r \le d-k$, then $\ker(A)=\ker(B) $.
In particular, the above lemmas imply that if $r>k$, then the answer is positive. Indeed, in that case, the kernels and images coincide, so we can consider the quotient operators: $\tilde A,\tilde B:V/D \to H$, where $D$ is the kernel, and $H$ is the image. Now $\tilde A, \tilde B$ are invertible operators between $r$-dimensional spaces, and they satisfy the assumption for $k<r$. Thus, by lemma 1, $\tilde A=\lambda \tilde B$, which implies $ A=\lambda B$.
Edit:
Here is a slick proof that the answer is positive in general:
Let $v\in V$ and let $X(v)$ be the collection of $k$-dimensional subspaces of $V$ that contain $v$. Then $$\text{span} \{v\}=\bigcap_{W\in X(v)}W,$$ so $$A(\text{span} \{v\})=A(\bigcap_{W\in X(v)}W) \subseteq \bigcap_{W\in X(v)}AW=\bigcap_{W\in X(v)}BW \subseteq B(\text{span} \{v\}),$$
where the last containment follows from this answer. This reduces the problem to the case where $k=1$.
Proof of Lemma 1:
Suppose that $A$ is invertible. Then, we have $SW=W$, where $S=A^{-1}B$. Thus, every $k$-dimensional subspace is $S$-invariant, which implies $S$ is a multiple of the identity.
Proof of Lemma 2: $\text{Image}(A)=\text{Image}(B)$.
Let $x=Av_1 \in \text{Image}(A)$; complete $v_1$ to a linearly independent set $v_1,\dots,v_k$. Then $$ x \in A(\text{span}\{v_1,\dots,v_k\})=B(\text{span}\{v_1,\dots,v_k\})\subseteq \text{Image}(B),$$
so $\text{Image}(A) \subseteq \text{Image}(B)$. The other direction follows by symmetry.
Proof of Lemma 3: If $r \ge k$ or $r \le d-k$, then $\ker(A)=\ker(B) $.
First, suppose that $r \ge k$, and let $v_1 \notin \ker A$. Complete $v_1$ into a linearly independent set $v_1,\dots,v_k$ such that $A(\text{span}\{v_1,\dots,v_k\})$ is $k$-dimensional. Then $B(\text{span}\{v_1,\dots,v_k\})$ is $k$-dimensional, so $Bv_1 \neq 0$. This shows $\ker(A)^c \subseteq \ker(B)^c$, i.e. $\ker(B)\subseteq \ker(A)$. The other direction follows by symmetry.
Now, suppose that $r \le d-k$. Then, since the nullity is $\ge k$, every $v_1 \in \ker B$ can be completed into a linearly independent set $v_1,\dots,v_k$, all in $\ker B$. This implies that $A(\text{span}\{v_1,\dots,v_k\})=0$, so $v_1 \in \ker A$.