Let $ \pi: H \to GL(V) $ be an irreducible representation. Define $ N_\pi^r(H) $ inductively by $$ N_\pi^{r+1}(H)=\{ g \in GL(V): g \pi(H) g^{-1} \subset N_\pi^r(H) \} $$ starting from $ N_\pi^1(H):= \pi(H) $.
Note that the set $ N_\pi^r(H) $ is generally not a group.
My question: Is $ N_\pi^r(H) $ closed under inverses?
Some thoughts: If $ \pi(H) $ is normal in $ GL(V) $ then $ N_\pi^r(H)=GL(V) $ for all $ r \geq 2 $ and the whole construction is trivial. So the question is only interesting if $ H $ is not a normal subgroup. It is certainly true for $ r=1 $ since groups are always closed under inverses.
Context:
This construction is used for a naturally occurring object called the Clifford hierarchy which appears in quantum computing. For example, the (single qubit) Clifford hierarchy is the case where $ V=\mathbb{C}^2 $ and $ H=\pi(H)= \left\langle \begin{bmatrix} 0 & 1 \\ 1 & 0 \end{bmatrix}, \begin{bmatrix} 1 & 0 \\ 0 & -1 \end{bmatrix} \right\rangle $ is the tautological representation of the single qubit Pauli group.
This is a follow-up question to Is this interesting set, defined in terms of conjugation, closed under inverses? which deals with the case of general groups, not representations.